- Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores
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The modified Debus-Radziszewski reaction was used to design and synthesize novel truxene derived blue-emitting materials bearing phenanthroimidazole substituents. The materials were prepared non-catalytically under ambient conditions using a triamino based derivative of truxene as a key precursor in good yields. The 5, 5′, 10, 10′, 15, and 15′ positions of the truxene were alkylated to provide solubility to the molecules, making the materials solution processable. The substituted phenanthroimidazole moieties were introduced at the 2, 7, 12 positions of truxene to synthesize the target molecules. Three new materials were prepared by varying the phenyl group attached at the C2 position of the phenanthroimidazole moiety, designated as PT1 for the phenyl, PT2 for the 4-methoxyphenyl, and PT3 for the 4-cyanophenyl substituent. From the photophysical studies, PT3 was found to have dominant charge transfer characteristics in its excited state. Also, PT3 exhibited a photoluminescence quantum yield as high as 0.83. The optimized geometries from the computational studies revealed that the molecules are highly twisted, with dihedral angles of ~75°. The HOMO-LUMO distributions were found to be well separated showing the bipolar characteristic of the compounds. The band gap values from computational studies were found to be in agreement with experimental values. The emission spectra in the solid state gave maxima at 402 nm for PT1, 412 nm for PT2, and 450 nm for PT3. The materials were thus found to be emitting in the blue region of the visible spectrum. The TCSPC and TRPL studies were carried out to explore further the excited states of the molecules, wherein radiative pathways were found to be dominant.
- Kaur, Banpreet,Moghe, Dhanashree,Kabra, Dinesh,Jacob, Josemon
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- Synthesis and photophysical properties of star-shaped blue green emitting π-conjugated spirotruxenes
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Here, we report a simple and useful strategy for a series of C3-symmetric π-conjugated and highly soluble spiro-annulated truxene derivatives. The role of substituent at C5, C10, C15, C2, C7, and C12 positions was studied. We observed that truxenes containing carbonyl groups showed red shift in the absorption maxima in comparison with compounds devoid of carbonyl group. Enhanced conjugation in these systems may be responsible for this red shift. It was observed that truxene derivatives with carbonyl moiety exhibited faster decay than other derivatives. Benzyl groups play some role in the excited state dynamics as decay becomes slower when the spiro moiety was replaced by benzyl group at C5, C10, and C15 positions. Additionally, we noticed the highest quantum yield in t-butanol solvent and least in acetonitrile.
- Kotha, Sambasivarao,Ali, Rashid,Panguluri, Nageswara Rao,Datta, Anindya,Kannaujiya, Krishna K.
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- Acceptor or donor (diaryl B or N)substituted octupolar truxene: Synthesis, structure, and charge-transfer-enhanced fluorescence
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(Graph Presented) Two diaryl B- and N-substituted truxene charge-transfer compounds B3 and N3 have been synthesized. The fluorescence intensities of several nonfunctionalized truxene compounds are 1 order of magnitude weaker than that of B3 and N3. To reveal the structure-property correlations, the X-ray structures of B3 and N3 and their precursors 3 and 4 have been determined. The extended molecular dimension, the especially shortened B-C bond, and the improved planarity of B3 can serve as direct structural evidence for the charge transfer.
- Yuan, Mao-Sen,Fang, Qi,Liu, Zhi-Qiang,Guo, Jian-Ping,Chen, Hong-Yu,Yu, Wen-Tao,Xue, Gang,Liu, Dian-Sheng
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- F?rster Energy Transport in Metal-Organic Frameworks Is beyond Step-by-Step Hopping
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Metal-organic frameworks (MOFs) with light-harvesting building blocks designed to mimic photosynthetic chromophore arrays in green plants provide an excellent platform to study exciton transport in networks with well-defined structures. A step-by-step exciton random hopping model made of the elementary steps of energy transfer between only the nearest neighbors is usually used to describe the transport dynamics. Although such a nearest neighbor approximation is valid in describing the energy transfer of triplet states via the Dexter mechanism, we found it inadequate in evaluating singlet exciton migration that occurs through the F?rster mechanism, which involves one-step jumping over longer distance. We measured migration rates of singlet excitons on two MOFs constructed from truxene-derived ligands and zinc nodes, by monitoring energy transfer from the MOF skeleton to a coumarin probe in the MOF cavity. The diffusivities of the excitons on the frameworks were determined to be 1.8 × 10-2 cm2/s and 2.3 × 10-2 cm2/s, corresponding to migration distances of 43 and 48 nm within their lifetimes, respectively. "Through space" energy-jumping beyond nearest neighbor accounts for up to 67% of the energy transfer rates. This finding presents a new perspective in the design and understanding of highly efficient energy transport networks for singlet excited states.
- Zhang, Qiongqiong,Zhang, Cankun,Cao, Lingyun,Wang, Zi,An, Bing,Lin, Zekai,Huang, Ruiyun,Zhang, Zhiming,Wang, Cheng,Lin, Wenbin
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- Cost-effective hole transporting material for stable and efficient perovskite solar cells with fill factors up to 82%
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A new small molecule-based hole selective material (HSM), 4,4′,4′′-(7,7′,7′′-(5,5,10,10,15,15-hexahexyl-10,15-dihydro-5H-diindeno[1,2-a:1′,2′-c]fluorene-2,7,12-triyl)tris(2,3-dihydrothieno[3,4-b][1,4]dioxine-7,5-diyl))tris(N,N-bis(4-methoxyphenyl)aniline) (TRUX-E-T), has been developed by a facile synthesis with reduced cost. The highest occupied molecular orbital energy level and lowest unoccupied molecular orbital energy level of TRUX-E-T are -5.10 and -2.50 eV, respectively, making it a suitable HSM for lead iodide perovskite solar cells. TRUX-E-T can be smoothly deposited onto perovskite layers, enabling efficient perovskite solar cells with thin TRUX-E-T layers (~50 nm), which helps cut the unit cost of the HSL used in PVSCs to approximately one-fortieth (1/40) of 2,2′,7,7′-tetrakis (N,N-di-p-methoxyphenylamino)-9,9′-spirobifluorene (spiro-OMeTAD). Additionally, TRUX-E-T exhibits hole mobilities as high as 2.47 × 10-4 cm2 V-1 s-1, better than spiro-OMeTAD. As a result, our perovskite solar cells using TRUX-E-T have shown high fill factors up to 82%. The champion cell achieved a maximum power conversion efficiency of 18.35% (16.44%) when measured under reverse (forward) voltage scan under AM1.5 G 100 mW cm-2 illumination. Our un-encapsulated cells exhibited good stability in ambient air, maintaining 96.4% of their initial efficiency of 18.35% after 20 days of storage.
- Guan, Lei,Yin, Xinxing,Zhao, Dewei,Wang, Changlei,An, Qiaoshi,Yu, Jiangsheng,Shrestha, Niraj,Grice, Corey R.,Awni, Rasha A.,Yu, Yue,Song, Zhaoning,Zhou, Jie,Meng, Weiwei,Zhang, Fujun,Ellingson, Randy J.,Wang, Jianbo,Tang, Weihua,Yan, Yanfa
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- Strong Ground- and Excited-State Charge Transfer in C3-Symmetric Truxene-Derived Phenothiazine-Tetracyanobutadine and Expanded Conjugates
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The C3-symmetric star-shaped phenothiazene-substituted truxene 1 was reacted with the electron acceptors tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). The cycloaddition–retroelectrocyclization reaction yields the conjugates 2 and 3. A combination of spectral, electrochemical, and photophysical investigations of 2 and 3 reveals that the functionalization of the triple bond has a pronounced effect on their ground and excited-state interactions. Specifically, the existence of strong ground-state interactions between phenothiazine and the electron-accepting groups results in charge-transfer states, while subsequent ultrafast charge separation yields electron transfer products. This is unprecedented not only in phenothiazine chemistry but also in tetracyanobutadiene- and dicyanoquinodimethane-derived donor–acceptor conjugates. Additionally, by manipulating spectroelectrochemical data, a spectrum of the charge-separated species is construed for the first time, and shown to be highly useful in interpreting the rather complex transient spectra.
- Sharma, Rekha,Thomas, Michael B.,Misra, Rajneesh,D'Souza, Francis
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- A Case Study on the Influence of Substitutes on Interlayer Stacking of 2D Covalent Organic Frameworks
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Interlayer stacking of 2D covalent organic frameworks (COFs) plays a crucial role in determining not only the geometry of channels inside COFs but also the mobility of carrier transport between COF layers. However, though topological structures of 2D COFs monolayers can be precisely predicted through the structures of building blocks, factors affecting their interlayer stacking remain poorly understood. In this work, a truxene-based building block on which six methyl groups are introduced was designed. The condensation of it with 1,4-diaminobenzene or benzidine afforded 2D COFs with the methyl groups extending out-of-plane of the layers. A significant influence of the methyl groups on interlayer stacking of the COFs was revealed by the adoption of inclined packing of monolayers, which has never been experimentally observed before. This unprecedented stacking manner was confirmed by powder X-ray diffraction analysis, pore-size distribution analysis, and TEM investigation.
- Fan, Yu,Wen, Qiang,Zhan, Tian-Guang,Qi, Qiao-Yan,Xu, Jia-Qiang,Zhao, Xin
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- Fusing three perylenebisimide branches and a truxene core into a star-shaped chromophore with strong two-photon excited fluorescence and high photostability
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A novel star-shaped chromophore, Tr-PBI, was constructed by fusing three perylenebisimide branches and a truxene core. Tr-PBI exhibits high photostability and excellent two-photon properties: the maximum of δTPA is 11000 GM at 990 nm and fluorescence quantum efficiency Φ is 0.40 in THF. The Royal Society of Chemistry 2012.
- Xie, Yuanpeng,Zhang, Xinfu,Xiao, Yi,Zhang, Youdi,Zhou, Fan,Qi, Jing,Qu, Junle
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- Synthesis of new truxene derivatives: Possible precursors of fullerene partial structures?
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Preparations of compound 4 and of truxene derivatives 5, 6a,b, 7, 8, 10a,b, 11, 12a,b, and 13a,b are described. These substances are potential starting materials for the synthesis of bowl shaped polyaromatic compounds containing structural elements of fullerenes.
- Dehmlow, Eckehard V.,Kelle, Torsten
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- Effective blocking of the molecular aggregation of novel truxene-based emitters with spirobifluorene and electron-donating moieties for furnishing highly efficient non-doped blue-emitting OLEDs
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Several truxene-based blue fluorescent emitters bearing different functional moieties and peripheral spirobifluorene groups have been successfully designed and synthesized. Through tuning the chemical structures and electronic characters of the functional moieties, both optimized molecular configuration and elevated highest occupied molecular orbital (HOMO) energy levels have been afforded to the truxene-based emitters, representing a new effective strategy for solving the problems of molecular aggregation and poor charge carrier injection/transport associated with the truxene-based blue emitters. Owing to the sophisticated strategy, the concerned emitters can furnish highly efficient non-doped blue-emitting OLEDs with a maximum current efficiency (ηL) of 7.41 cd A-1, an external quantum efficiency (ηext) of 4.33%, and a power efficiency (ηP) of 6.79 lm W-1, representing the state-of-the-art EL efficiencies ever achieved by the truxene-based blue emitters. All promising results will not only show the great potential of the concerned truxene-based blue fluorescent emitters in the field of OLEDs, but also furnish valuable clues for developing high-performance truxene-based emitters.
- Yao, Chunliang,Yu, Yue,Yang, Xiaolong,Zhang, Huiming,Huang, Zuan,Xu, Xianbin,Zhou, Guijiang,Yue, Ling,Wu, Zhaoxin
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- C 3-Symmetric star shaped donor-acceptor truxenes: Synthesis and photophysical, electrochemical and computational studies
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This manuscript reports the design and synthesis of C3-symmetric star shaped donor and acceptor substituted truxenes 6, 7, 10 and 11 using Pd-catalyzed Sonogashira cross-coupling and [2+2] cycloaddition-retroelectrocyclization reactions. Their photophysical, electrochemical and computational studies were explored, which indicate strong donor-acceptor interactions and effective tuning of the HOMO-LUMO gap. The computational studies reveal that the TCNE and TCNQ substituted truxenes 10 and 11 exhibit lower HOMO-LUMO gaps compared to truxenes 6 and 7. The reaction pathway of [2+2] cycloaddition-retroelectrocyclization was studied using computational calculations, which reveal that the donor substituted truxene 7 is favourable for cycloaddition-retroelectrocyclization reactions, whereas acceptor substituted truxene 6 is not favourable.
- Sharma, Rekha,Maragani, Ramesh,Misra, Rajneesh
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- Supramolecular Coordination of Pb2+ Defects in Hybrid Lead Halide Perovskite Films Using Truxene Derivatives as Lewis Base Interlayers
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Truxene derivatives, due to their molecular structure and properties, are good candidates for the passivation of defects when deposited onto hybrid lead halide perovskite thin films. Moreover, their semiconductor characteristics can be tailored through the modification of their chemical structure, which allows-upon light irradiation- the interfacial charge transfer between the perovskite film and the truxene molecules. In this work, we analysed the use of the molecules as surface passivation agents and their use in complete functional solar cells. We observed that these molecules reduce the non-radiative carrier recombination dynamics in the perovskite thin film through the supramolecular complex formation between the Truxene molecule and the Pb2+ defects at the perovskite surface. Interestingly, this supramolecular complexation neither affect the carrier recombination kinetics nor the carriers collection but induced noticeable hysteresis on the photocurrent vs voltage curves of the solar cells under 1 sun illumination.
- Aktas, Ece,Jiménez-López, Jesús,Rodríguez-Seco, Cristina,Pudi, Rajesh,Ortu?o, Manuel A.,López, Núria,Palomares, Emilio
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- Star-shaped electron acceptors containing a truxene core for non-fullerene solar cells
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A series of new electron acceptors containing a truxene core with intense optical absorption were synthesized and used for non-fullerene organic solar cells. Due to the weak electron-donating characteristic of truxene core and thereby weak intramolecular charge transfer interaction from electron-donating core to electron-withdrawing end groups, the resulting new acceptors show relatively wide optical band-gap and high-lying lowest unoccupied molecular orbitals (LUMOs), which consequently lead to complementary light spectra with narrow band-gap donor polymers and high open circuit voltage (Voc) in solar cells. Particularly, Tr(Hex)6-3BR, a star-shaped planar acceptor, produced the highest power conversion efficiency of 2.1% with a high Voc of 1.02 V when blended with PTB7-Th.
- Lin, Kaiwen,Xie, Boming,Wang, Zhenfeng,Xie, Ruihao,Huang, Yunping,Duan, Chunhui,Huang, Fei,Cao, Yong
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- A Cavity-Tailored Metal-Organic Cage Entraps Gases Selectively in Solution and the Amorphous Solid State
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Here we report the subcomponent self-assembly of a truxene-faced Zn4L4 tetrahedron, which is capable of binding the smallest hydrocarbons in solution. By deliberately incorporating inward-facing ethyl groups on the truxene faces, the resulting partially-filled cage cavity was tailored to encapsulate methane, ethane, and ethene via van der Waals interactions at atmospheric pressure in acetonitrile, and also in the amorphous solid state. Interestingly, gas capture showed divergent selectivities in solution and the amorphous solid state. The selective binding may prove useful in designing new processes for the purification of methane and ethane as feedstocks for chemical synthesis.
- Zhu, Jun-Long,Zhang, Dawei,Ronson, Tanya K.,Wang, Wenjing,Xu, Lin,Yang, Hai-Bo,Nitschke, Jonathan R.
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- A simple synthesis of truxene, a building block for optoelectronics and fullerene fragments
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Truxene was efficiently synthesized by reduction of truxenone with excess hydrazine hydrate in diethylene glycol at 180 C without added base, a variation of the Huang-Minlon Wolff-Kishner reduction. The proposed mechanism highlights hydrazine as a nucleophile and a base, extracting protons from the hydrazone and diazene intermediates.
- Oded, Yaacov Netanel,Agranat, Israel
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- Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools
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Design, synthesis and properties of polycyclic aromatic hydrocarbons (PAHs) has historically attracted a considerable interdisciplinary interest from both fundamental as well as applied viewpoint on account of their wonderful optoelectronic properties. The scientific interest in two-dimensional star-shaped PAHs particularly in truxene architectures arises because of their high thermal stability, exceptional solubility and ease with which they can be constructed and modified. Therefore, bearing in mind a wide range of applications of truxene and its congeners, herein we reveal three novel distinctly different routes for the generation of C3-symmetric pyrrole-based truxene architectures by means of cyclotrimerization, ring-closing metathesis (RCM), Clauson–Kaas and Ullmann-type coupling reactions as key steps. Moreover, we have also assembled some other interesting heterocyclic systems possessing oxazole, imidazole, benzimidazole, and benzoxazole in the framework of truxene. Additionally, the preliminary photophysical properties (absorption and emission) for these versatile systems has been revealed.
- Ali, Rashid,Alvi, Shakeel
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p. 1374 - 1384
(2021/06/16)
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- Star-shaped oligofluorene truxene macromolecules - Synthesis and properties as a function of alkyl chain length
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Star-shaped oligofluorene truxenes are very promising materials and have demonstrated excellent properties as the gain medium in organic semiconductor lasers (OSLs).1-10 Alkyl chains in oligofluorene truxenes act as solubilizing groups as well as spacers to prevent intermolecular π-π stacking that leads to quenching of the light emission. A new series of star-shaped systems analogous to hexyl oligofluorene truxenes11 with alkyl chains of different lengths (butyl chains and octyl chains) was synthesized. The objective of this study was to investigate the effect of alkyl chain length on the film-forming properties of oligofluorene-truxene materials and, as a result, on their optoelectronic properties for applications as the gain medium in OSLs.
- Kanibolotsky, Alexander L.,Orofino, Clara,Skabara, Peter J.
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- An expeditious and highly efficient synthesis of substituted pyrroles using a low melting deep eutectic mixture
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An expeditious green method for the synthesis of diverse valued substituted pyrroles through a Paal-Knorr condensation reaction, using a variety of amines and 2,5-hexanedione/2,5-dimethoxytetrahydrofuran in the presence of a low melting mixture ofN,N’-dimethylurea andL-(+)-tartaric acid (which acts as a dual catalyst/solvent system), has fruitfully been revealed. Herein, we have disclosed the applicability of this simple yet effective strategy for the generation of mono- and dipyrroles in good to excellent yields. Moreover,C3-symmetric tripyrrolo-truxene derivatives have also been assembled by means of cyclotrimerization, Paal-Knorr and Clauson-Kaas reactions as crucial steps. Interestingly, the melting mixture was recovered and reused with only a gradual decrease in the catalytic activity (over four cycles) without any significant drop in the yield of the product. This particular methodology is simple, rapid, environmental friendly, and high yielding for the generation of a variety of pyrroles. To the best of our knowledge, the present work reveals the fastest greener method reported up to this date for the construction of substituted pyrroles by utilizing the Paal-Knorr synthetic protocol, achieving impressive yields under operationally simple reaction conditions without involving any precarious/dangerous catalysts or unsafe volatile organic solvents.
- Alvi, Shakeel,Ali, Rashid
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p. 9732 - 9745
(2021/12/01)
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- Gas transport properties of truxene-based network polyimide membrane with flexible hexyl side chains
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Crosslinking is a viable way to construct the network polymers which possesses the merits of high rigidity, excellent plasticization resistances, and good thermal stability using in the area of gas separation. However, dependence on crosslinking method often leads to contracted pores among polymer chains and in turn, sacrifices gas permeability seriously. In this work, a novel truxene triamine monomer with flexible hexyl side chains (termed as HTUTA) was designed, synthesized, and subsequently reacted with three different dianhydrides ODPA, BTDA, and 6FDA though polycondensation to obtain a series of network polyimides (PIs) membranes. Among these three designed truxene-based network PIs, HTUTA-6FDA had the best overall gas separation performance rooting from its bulky –C(CF3)2- moieties within the polymer framework. Compared with our previous reported TAPA-6FDA and TAPB-6FDA, the overall gas transport properties of the newly designed truxene-based network PIs are enhanced obviously because of incorporating the bulky and flexible side chains as well as enhancing the polymer backbone rigidity via using the truxene structure as the building block. For instance, the gas permeability of designed HTUTA-6FDA for CO2 and O2 were, respectively, enhanced 261% and 253% in comparison with these of TAPB-6FDA. In addition, benefiting from the flexible hexyl side chains, the partial chain segment motion was increased and accordingly the inter- and intra-chain interactions were minimized. Thus, a broad operating flexibility without the risk of gelation could be achieved during the tridimensional polycondensation process, which is extremely significant to their practical production. We hope this study can open a new insight into the rational design of the network PI membranes with enhanced gas permeability as well as no risk of gelation trend before film-forming.
- Liu, Xiangyun,Luo, Jiangzhou,Wang, QingQing,Xue, Song,Zong, Xueping
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- ORGANIC COMPOUNDS, AND LIGHT EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUNDS
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The present disclosure relates to an organic compound having a fused aromatic or hetero aromatic ring including a carbazole or fluorene moiety and a group having excellent charge mobility property, and a light emitting diode and a light emitting device having the organic compound. The organic compound can be applied into the light emitting diode by using solution process and has very deep HOMO energy level. When the organic compound is applied into a chare transfer layer, a HOMO energy level bandgap between the charge transfer layer and an emitting material layer is reduced so that holes and electrons can be injected into the emitting material layer in a balanced manner.
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Paragraph 0223-0226
(2020/07/02)
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- ORGANIC COMPOUND, LIGHT EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUND
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The present disclosure relates to an organic compound having a fused aromatic or hetero aromatic ring including a carbazole or fluorene moiety and a group having excellent charge mobility property, and a light emitting diode and a light emitting device having the organic compound. The organic compound can be applied into the light emitting diode by using solution process and has very deep HOMO energy level. When the organic compound is applied into a chare transfer layer, a HOMO energy level bandgap between the charge transfer layer and an emitting material layer is reduced so that holes and electrons can be injected into the emitting material layer in a balanced manner.
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Paragraph 0198-0199
(2020/07/05)
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- Truxene-based starlike symmetrical organic solar battery micromolecule acceptor material and its preparation method and organic solar battery
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The invention discloses a truxene-based starlike symmetrical organic solar battery micromolecule acceptor material and its preparation method and an organic solar battery. The material is formed by copolymerizing an electrondrawing group, a bridging unit and a truxene structure unit. The material is a typical D-pi-A structure, and the D-A effect can make the structure more stable; the spectrum hasred shift; thus the problem of low wavelength of the ultraviolet absorption of the truxene itself is solved, thus the material can absorb more solar spectrums, and the conversion efficiency is further improved; meanwhile, the material has unique starlike symmetrical structure, and is good in planarity, high in absorbing coefficient; the absorbing ability of the solar light is enhanced, and the demand of the high-efficiency device is satisfied; truxene-based starlike symmetrical organic solar battery micromolecule acceptor material has huge application prospect in solar battery field, in particular to the activity layer of the solar battery.
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Paragraph 0067; 0068; 0069; .0070
(2018/07/30)
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- Design and synthesis of spirotruxene and spirofluorene derivatives
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The work presented here describes a facile and efficient method for the synthesis of spirotruxene and spirofluorene compounds using allylation and RCM as key steps from readily available starting materials.
- Kotha, Sambasivarao,Ali, Rashid,Panguluri, Nageswara Rao,Deb, Ashoke Chandra
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p. 1489 - 1492
(2019/05/21)
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- One-step, large-scale synthesis of isotruxene
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A concise procedure for the one-step synthesis of isotruxene has been developed. Isotruxene is obtained in around 60% yield on a 150-gram scale through acid-catalysed cyclotrimerisation of equimolar amounts of 1-indanone and 2-indanone. The separation procedure is convenient and is based on different solubilities between isotruxene and side products.
- Zhou, Cen,Xuan, Wei,Luo, Shi-Peng,Bao, Yue-Hua
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p. 556 - 557
(2018/11/27)
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- Aromatic azoxybenzene compound and preparation method thereof
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The invention discloses an aromatic azoxybenzene compound and a preparation method thereof. The preparation method comprises the following steps: firstly reducing aromatic nitro-compounds into azoxybenzene through photoinduction in an alkaline condition; firstly synthesizing different aromatic nitro-compounds; secondly, carrying out nitro reduction under the irradiation of a xenon lamp under the conditions of potassium hydroxide, methylbenzene and isopropyl alcohol, and thus synthesizing the aromatic azoxybenzene compound. The preparation method disclosed by the invention has the advantages of simple components, mild reaction conditions, low toxicity, environmental protection, high selectivity and the like; the obtained aromatic azoxybenzene compound has potential application in the aspects of dyes, liquid crystal materials, optical materials and the like.
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Paragraph 0021; 0027
(2017/10/25)
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- The star-shaped symmetrically polyindene-based organic electroluminescent material and its preparation method
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The invention discloses a truxene-based star-shaped symmetric organic electroluminescence material and a preparation method thereof. A synthesis route of the material comprises three steps: (1) synthesizing a central structure which takes truxene as a main body; (2) introducing an aryl bridging unit through suzuki reaction; (3) introducing periphery functional groups through suzuki reaction. The material adopts a unique star-shaped symmetric structure, the steric-hinerance effect of the material is remarkably improved, and the amorphous form of the material is improved, so that the problem of recrystallization aging of an organic photoelectric device is effectively prevented; due to the unique star-shaped structure, the molecule piling is effectively reduced, the fluorescence quenching caused by molecule piling is prevented, and the efficiency of an organic electroluminescence device is improved.
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Paragraph 0047
(2017/01/26)
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- Synthesis and characterization of hole-transporting star-shaped carbazolyl truxene derivatives
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Two star-shaped carbazolyl truxene derivatives (1 and 2) are synthesized via iodination of truxene and Cu-catalyzed C-N coupling with carbazole or 3,6-di(9-carbazolyl)carbazole. In solution phase, these compounds show maximum absorption bands around 330 nm and the emission maxima at 367 and 391 nm. The emission bands shift bathochromically in solid phase as a result of the more restricted molecular vibration and rotation. Both compounds show good thermal stabilities with glass transition temperatures at 249 and 293 °C and 5% weight loss temperatures at 392 and 371 °C, respectively. Both compounds exhibit good hole-transporting properties as the devices of structure ITO/PEDOT:PSS/1 or 2/Alq3/LiF:Al could provide maximum brightness of 12 000 cd m-2 with turn-on voltages of 3.1-4.1 V, and maximum external quantum efficiency of 0.89-1.13%.
- Raksasorn, Danusorn,Namuangruk, Supawadee,Prachumrak, Narid,Sudyoadsuk, Taweesak,Promarak, Vinich,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
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p. 72841 - 72848
(2015/09/15)
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- Synthesis of precursors for large-diameter hemispherical buckybowls and precursors for short carbon nanotubes
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We report herein the synthesis of six precursor molecules for the rational synthesis of isomerically pure armchair, zigzag, or chiral single-walled carbon nanotubes (SWCNTs). The polycyclic aromatic hydrocarbons possess the required carbon connectivity for the generation of extended hemispherical buckybowls with predefined geometry through intramolecular cyclodehydrogenation. The precursors for the short carbon nanotubes and the large-diameter hemispherical buckybowls have potential for the rational initiation of single-chirality SWCNT growth on metal surfaces. The options for the construction of precursors for various SWCNT chiralities based on the suggested synthesis strategy are presented.
- Mueller, Andreas,Amsharov, Konstantin Yu.
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p. 6155 - 6164,10
(2020/09/16)
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- Water-soluble anionic fluorophores from truxene
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Two new water-soluble fluorophores are synthesized from truxene and ester-substituted aryl acetylenes. The truxene core is decorated by 2-(2′-methoxy)ethoxyethyl groups to enhance the hydrophilicity of these fluorophores as well as to prevent the aggregation by π-stacking in aqueous media. The conjugated structures are assembled by iodination of the truxene core and subsequent Sonogashira coupling with aryl acetylenes. Upon the hydrolysis of the ester groups, water-soluble fluorophores are obtained in good to excellent yield (30-71% for 3 steps). A photophysical investigation reveals that these compounds exhibit strong fluorescence signals (quantum yield 46-63%) with maximum emission wavelength around 390-400 nm in aqueous phosphate buffer. Preliminary screening on sensing application shows that their fluorescent signals can be selectively quenched by porphyrin-containing metalloproteins.
- Earmrattana, Nopporn,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
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experimental part
p. 1428 - 1433
(2012/03/27)
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- Synthesis of a higher fullerene precursor - An "unrolled" C 84 fullerene
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We report the synthesis of the C84(20)-fullerene related hydrocarbon C84H42, which possesses more than 83% of the C84(20)-fullerene connectivity, and its selective transformation to C84 by flash vacuum pyrolysis (FVP). The Royal Society of Chemistry 2009.
- Amsharov, Konstantin,Jansen, Martin
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scheme or table
p. 2691 - 2693
(2009/09/29)
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- Trisannulated benzene derivatives by acid catalyzed aldol cyclotrimerizations of cyclic ketones. methodology development and mechanistic insight
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(Chemical Equation Presented) Several factors that contribute to the success of aldol cyclotrimerizations have been clarified as part of an effort to shed light on the inner workings of this century old reaction. The use of 4,7-di-tert-butylacenaphthenone (11) as a mechanistic probe molecule has led to intriguing discoveries about temperature, solvent, and solubility effects. Solvents that are both polarizable and somewhat polar, e.g., o-dichlorobenzene (ODCB), work best for the aromatic ketones examined. Certain Bronsted acids were found to work better than Lewis acids as catalysts for the archetypal aldol cyclotrimerization of indanone (2) in aprotic solvents, and a strong dependence on the pKa of the acid was observed. A standardized protocol, using p-toluenesulfonic acid monohydrate, is shown to work well in a number of test cases.
- Amick, Aaron W.,Scott, Lawrence T.
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p. 3412 - 3418
(2008/02/03)
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- Rhodium-catalyzed direct aldol condensation of ketones: A facile synthesis of fused aromatic compounds
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Cationic rhodium complex [Cp*Rh(η6-C6H 6)](BF4)2 (1) acts as an efficient catalyst for direct aldol condensation of ketones. The method can be applied to one-pot synthesis of fused aromatic compounds from cyclic ketones via sequential C-C bond formations.
- Terai, Hiroki,Takaya, Hikaru,Naota, Takeshi
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p. 1705 - 1708
(2007/10/03)
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- Attempted Preparation of Sulfonioindenides
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3-(Methylthio)indene (13), obtained from lithium 1-indenide (10) and dimethyl disulfide (11), reacts with methyl iodide to form truxene (14) and with methyl fluorosulfonate to form 2-(3-indenyl)-3-(methylthio)indene (16).Nucleophilic substitution of 1-chloro-2,3-dimethyl-5,6-(methylenedioxy)indene (22) with thiolates allows the isolation of the thioethers 23A/23B, which were alkylated with trialkyloxonium salts to give the stable sulfonium tetrafluoroborates 24.Deprotonation of 24 leads to extensive decomposition.The thioethers 28 have been prepared from 2-indanone (26).Their alkylation leads to the formation of (2-indenyl)sulfonium tetrafluoroborates 29.Deprotonation of 29a yields 2-(dimethylsulfonio)indenide (6), characterized by NMR spectroscopy.
- Hartke, Klaus,Schilling-Pindur, Annegret
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p. 552 - 563
(2007/10/02)
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- Sulfur Compounds in Crude Oil, II - 6,11-Dihydrodiindenothiophenes
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Ring closures with 3,5-diphenyl-2,4-thiophenedicarboxylic acid and theirderivates 2 have been studied.Ring closure to the indenothiophene system 3 occurs with identical functional groups in the 2- and 4-position at the thiophene ring.The indenothiophene system 4 is the reaction product from methyl 5-chloroformyl-2,4-diphenyl-3-thiophenecarboxylate with the more reactive functional group in the 5-position at the thiophene ring.The indenothiophene 4b is the starting material for 6,11-dihydrodiindenothiophenes 5.The with truxenecontaminated parent compound 5 is also obtained from 3,5-diphenyl-2,4-thiophenedimethanol (2f) with polyphosphoric acid.
- Boberg, Friedrich,Czogalla, Claus-Detlef,Schroeder, Juergen
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p. 1588 - 1597
(2007/10/02)
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- Sulfur Compounds in Crude Oil, III - Dihydrodiindenothiophenes
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Syntheses to the dihydrodiindenothiophenes 1 - 3 have been studied. 1-3 were prepared by thermolysis of 8H-indeno-1,2,3-thiadiazole (10) or 4H-indeno-1,2,3-thiadiazole (13) or by reduction of the corresponding diketones 17, 19, and 21 which were obtained by thermolysis of indeno-1,2,3-thiadiazol-8-one (16) or from 2,3-dichloroinden-1-one (23) with Na2S.Mechanisms with analogous intermediates explain the formation of the indenothiophenes. - Another synthesis of indenothiophene-10,11-dione (21) starts from 2,5-diphenyl-3,4-thiophenedicarboxylic acid (29). - 10,11-Dihydrodiindenothiophene (3) is the known sulfurization product of hydrindene, the structure of 3 is corrected.
- Boberg, Friedrich,Czogalla, Claus-Detlef,Torges, Karl-Franz,Wentrup, Gerhard-Juergen
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p. 1598 - 1607
(2007/10/02)
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