- Rational bridging affording luminogen with AIE features and high field effect mobility
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Linear and starburst emissive materials constructed by multiple triphenylamine (TPA) groups are extensively used in optoelectronic devices owing to their luminescence and good charge transport properties. Usual connecting units such as single bonds and be
- Zhao, Lifang,Lin, Yiliu,Liu, Tong,Li, Hongxiang,Xiong, Yu,Yuan, Wang Zhang,Sung, Herman H.-Y.,Williams, Ian D.,Zhang, Yongming,Tang, Ben Zhong
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- Synthesis and characterization of diphenylamine derivative containing malononitrile for thermally activated delayed fluorescent emitter
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To increase the efficiency of blue organic light-emitting diodes (OLEDs), new blue dopants, 2-(bis(4-(diphenylamino)phenyl)methylene)malononitrile (4-DPM) and 2-(bis(3-(diphenylamino)phenyl) methylene)malononitrile (3-DPM), with thermally activated delayed fluorescence were synthesized. 4-DPM with a p-phenyl linker between the electron-donating diphenylamine unit and the electron-withdrawing malonitrile unit showed a large overlap in the phenyl linker as well as the malonitrile unit, while 3-DPM with an m-phenyl linker showed a weak overlap in the phenyl linker. The OLED with the 3-DPM dopant showed higher efficiencies of 12.62?cd/A and 8.81?lm/W compared to that with the 4-DPM dopant (1.38?cd/A and 0.70?lm/W). This result was attributed to the small overlap between the electron-donating and electron-withdrawing units, the small charge-transfer singlet-triplet state splitting below 0.1?eV, and the well-aligned structure in the horizontal direction, as determined by grazing incidence X-ray diffraction.
- Sohn, Sunyoung,Hyun Koh, Bong,Baek, Jae Yeul,Chan Byun, Hyun,Lee, Jae Hyun,Shin, Dong-Seon,Ahn, Hyungju,Lee, Han-Koo,Hwang, Jaeyoung,Jung, Sungjune,Kim, Yun-Hi
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- Corannulene-Incorporated AIE Nanodots with Highly Suppressed Nonradiative Decay for Boosted Cancer Phototheranostics In Vivo
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Fluorescent nanoparticles (NPs) based on luminogens with aggregation-induced emission characteristic (AIEgens), namely AIE dots, have received wide attention because of their antiquenching attitude in emission and reactive oxygen species (ROS) generation when aggregated. However, few reports are available on how to control and optimize their fluorescence and ROS generation ability. Herein, it is reported that enhancing the intraparticle confined microenvironment is an effective approach to advanced AIE dots, permitting boosted cancer phototheranostics in vivo. Formulation of a “rotor-rich” and inherently charged near-infrared (NIR) AIEgen with 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] and corannulene-decorated PEG affords DSPE-AIE dots and Cor-AIE dots, respectively. Compared to DSPE-AIE dots, Cor-AIE dots show 4.0-fold amplified fluorescence quantum yield and 5.4-fold enhanced ROS production, because corannulene provides intraparticle rigidity and strong interactions with the AIEgen to restrict the intramolecular rotation of AIEgen to strongly suppress the nonradiative decay and significantly facilitate the fluorescence pathway and intersystem crossing. Thus, it tremendously promotes phototheranostic efficacies in terms of NIR image-guided cancer surgery and photodynamic therapy using a peritoneal carcinomatosis-bearing mouse model. Collectively, it not only provides a novel strategy to advanced AIE dots for cancer phototheranostics, but also brings new insights into the design of superior fluorescent NPs for biomedical applications.
- Gu, Xinggui,Zhang, Xiaoyan,Ma, Huili,Jia, Shaorui,Zhang, Pengfei,Zhao, Yanjun,Liu, Qian,Wang, Jianguo,Zheng, Xiaoyan,Lam, Jacky W. Y.,Ding, Dan,Tang, Ben Zhong
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- Propeller-like D-π-A architectures: Bright solid emitters with AIEE activity and large two-photon absorption
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Two novel molecules TABzPA and TATpPA with D-π-A structure and large π-conjugation have been synthesized via Wittig reaction. Unlike common molecules, which exhibit the aggregation-caused quenching (ACQ) phenomenon, TABzPA and TATpPA exhibit aggregation-induced emission enhancement (AIEE) activity: weak luminescence in common solvents but strong emission when aggregated as nanoparticles and solid powders. Due to their intramolecular charge transfer (ICT) attribution and AIEE features, TABzPA and TATpPA display bathochromic effects. Combining ICT and AIEE features, these molecules are intensely yellow solid emitters with high quantum efficiencies of about 23.2% and 24.1%. Moreover, TABzPA and TATpPA have excellent two-photon absorption (2PA) properties owing to good planarity and large π-conjugation. The values of 2PA cross sections at 800 nm are 7590 GM and 7648 GM. The excellent optical properties of TABzPA and TATpPA pave the way for future potential applications in biophotonics and optoelectronics. This journal is the Partner Organisations 2014.
- Huang, Wei,Wang, Huan,Sun, Lu,Li, Bo,Su, Jianhua,Tian, He
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- Control of Multicolor and White Emission by Adjusting the Equilibrium between Fluorophores, Lewis Acids, and Their Complexes in Polymers
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Multicolor emissive materials consisting of a single luminophore, a Lewis acid, and their complex were developed. The emission colors can be tuned by changing the concentration of the solution and the ratio of mixed solvents. Various emission colors in the solid state were observed when the complexes were added to polymers in different amounts. The color change is due to equilibrium disruption between the single luminophore, the Lewis acid, and the complex thereof. White emission was observed by appropriately controlling the equilibrium by changing the amount of the complex in the polymer.
- Mori, Toshiaki,Yoshigoe, Yusuke,Kuninobu, Yoichiro
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supporting information
p. 14457 - 14461
(2019/09/17)
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- Synthesis, Structure, and Properties of Amino-Substituted Benzhydrylium Ions – A Link between Ordinary Carbocations and Neutral Electrophiles
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Optimized synthetic procedures for the straightforward access to eleven amino-substituted diarylmethylium tetrafluoroborates are described. These benzhydrylium ions cover a range of seven orders of magnitude in electrophilicity and provide a link between ordinary carbocations and neutral electrophiles. Five of these highly stabilized benzhydrylium tetrafluoroborates were characterized by single-crystal X-ray crystallography. While the experimentally determined bond lengths and angles in the solid state perfectly agree with those calculated by DFT methods for the gas phase and aqueous solution, crystal packing accounts for large differences in the twist angles of the aryl groups found in the solid state as compared to calculated structures.
- Mayer, Robert J.,Hampel, Nathalie,Mayer, Peter,Ofial, Armin R.,Mayr, Herbert
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supporting information
p. 412 - 421
(2018/09/14)
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- Organic compound having tetrahedron-like configuration
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The present invention relates to an organic compound having a tetrahedron-like configuration, wherein the organic compound has a structure represented by the following general formula (I) defined in the specification, A1-A4 are respectively and independently an unsaturated five-membered ring or an unsaturated six-membered ring, B is a direct bond , -C, -O-, -N-, -S-, or -C=C-, m is 0 or 1, Ris hydrogen, fluorine, substituted or unsubstituted C1-C12 alkyl, or substituted or unsubstituted C6-C12 aryl, and n is an integer of 0-2. The organic compound of the present invention has excellentphotoelectric property.
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Paragraph 0196; 0198; 0199
(2018/07/07)
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- Crystallization-induced phosphorescence, remarkable mechanochromism, and grinding enhanced emission of benzophenone-aromatic amine conjugates
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Pure organic luminogens with efficient room temperature phosphorescence (RTP) and remarkable mechanochromism are highly desired in view of their fundamental significance and technical applications. Herein, four twisted pure organic luminogens based on ben
- Luo, Weijian,Zhang, Yiren,Gong, Yongyang,Zhou, Qing,Zhang, Yongming,Yuan, Wangzhang
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supporting information
p. 1533 - 1536
(2018/08/24)
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- A novel D-A-D-A-D type molecule based on substituted dihydroindolo [3, 2-b] carbazole with large two-photon absorption cross section and excellent aggregation-induced enhanced emission property
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Two novel D-A-D-A-D type molecules T1 and T2 based on substituted dihydroindolo [3, 2-b] carbazole with large two-photon absorption (2PA) cross section and excellent aggregation-induced enhanced emission (AIEE) property have been synthesized and characterized. Both compounds emit weakly fluorescent in THF, while a significant AIEE property is observed in water/THF (v/v 50%/50%) for T1 and water/THF (v/v 90%/10%) for T2 with a sharp increase in fluorescence intensity. The solid fluorescence of T1 and T2 is located at 575 nm and 588 nm, and their quantum efficiencies are determined to be 3.2% and 5.8%, respectively. The corresponding 2PA cross section values for T1 and T2 at 800 nm are 867 GM and 1300 GM by the open-aperture Z-scan technique. These excellent performances of both compounds make them as attractive alternatives for biophotonic and optoelectronic applications.
- Tian, Guojian,Xiang, Ning,Zhou, Haitao,Li, Yiru,Li, Bo,Wang, Qiaochun,Su, Jianhua
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p. 298 - 303
(2015/12/30)
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- Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights
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Five hole-transporting triphenylamine derivatives containing methoxy and methyl groups are synthesized and investigated. The hole-mobility increases in the presence of methyl and methoxy substituents, exceeding 10-2 cm2 V-1 s-1 in the case of methyl groups. Quantum mechanical calculations on these compounds indicate very different dipole moments and intermolecular interaction strengths, with intriguing correlations with the trend in hole-mobility. Temperature dependent hole-mobility measurements indicate disorder dominated hole transport. The values of the energetic disorder parameter (σ) decrease upon methyl and methoxy substitutions despite the increase in dipole moments. This trend is discussed as a function of the interaction energy between adjacent molecules, the dipole moment, the molecular polarizability, and the conformational degree of freedom. Our results indicate that the global decrease of σ upon methyl and methoxy substitutions is dominated by the larger decrease in the geometrical randomness component of the energetic disorder. A direct correlation is established between the decrease in geometrical randomness and the increase in intermolecular interaction energies, mainly stemming from the additional C-H?π, O, N hydrogen bonds induced by methyl and methoxy groups.
- Mimaite, Viktorija,Grazulevicius, Juozas Vidas,Laurinaviciute, Rasa,Volyniuk, Dmytro,Jankauskas, Vygintas,Sini, Gjergji
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p. 11660 - 11674
(2015/11/17)
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- Large cyano- and triazine-substituted D-π-A-π-D structures as efficient AIEE solid emitters with large two-photon absorption cross sections
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A series of new large π-conjugated molecules including diphenylamine and carbazole have been synthesized and characterized (3a-c). All compounds display aggregation-induced emission enhancement (AIEE) characteristics: exhibiting weak fluorescence in pure
- Huang, Wei,Tang, Fansheng,Li, Bo,Su, Jianhua,Tian, He
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p. 1141 - 1148
(2014/02/14)
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- New cyano-substituted organic dyes containing different electrophilic groups: Aggregation-induced emission and large two-photon absorption cross section
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Three aggregation-induced emission active dyes (3a-c) were synthesized and their one- and twophoton absorption properties have been investigated. They were all found to be weakly fluorescent in THF solution, while they exhibited dramatic fluorescence enhancement in water/THF mixtures. The solid fluorescence of 3a-c was recorded and their fluorescence quantum efficiency (φf) values were determined to be 8.0%, 8.1%, and 16.4%, respectively. Moreover, the two-photon absorption (2PA) crosssections (σ) of 3a-c were measured and 3a showed the highest value of 702 GM The excellent aggregation-induced emission and 2PA properties provide a promising alternative for biophotonic materials.
- Zhou, Haitao,Huang, Wei,Ding, Li,Cai, Shengyun,Li, Xin,Li, Bo,Su, Jianhua
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p. 7050 - 7056
(2015/03/14)
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- New thermally stable cyano-substituted D-A-π-A-D molecules with aggregation-induced emission and large two-photo absorption cross-sections
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In this work, we have designed and synthesized a series of aggregation-induced emission active compounds (4a-c) via Suzuki coupling reaction. Their one and two-photon absorption properties have been investigated. These compounds exhibit high thermal stability, losing only 5% of their weights when heated to 482-503 °C in air. All compounds are quite weakly fluorescent in THF, while a significant AIE effect is observed in water/THF (v/v 70%/30%) mixtures with a sharp increase in fluorescence intensity (about 86, 42, and 103 times, orange, deep yellow and green, respectively). The solid fluorescence of 4a-c is located at 590, 579 and 547 nm, and their ΦF values are determined to be 9.2%, 2.4%, and 14.5%, respectively. Besides, the two-photon absorption (2PA) cross-sections of 4a-c were also measured by open aperture Z-scan technique, at the wavelength of 800 nm. The excellent aggregation-induced emission and 2PA cross-sections properties of 4a-c promote them as attractive candidates for biophotonic materials.
- Huang, Wei,Zhou, Haitao,Li, Bo,Su, Jianhua
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p. 3038 - 3045
(2013/04/24)
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- Novel organic dyes based on bulky tri(triphenylamine)-substituted styrene for dye-sensitized solar cells
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Three novel donor-π-acceptor (D-π-A) metal-free organic dyes (TB, TS and TF) based on tri(triphenylamine)-substituted styrene as donor with various conjugated linkers (benzene, thiophene and furan) were synthesized, characterized and used for the application of dye-sensitized solar cells (DSSCs). Under the same condition, The photo-to-electrical conversion efficiency of the DSSCs sensitized with TB, TS and TF reach 1.84%, 4.10% and 4.52%, respectively, which are lower than that sensitized with R1 (5.02%) with one triphenylamine unit. The results suggest that these bulky donor-based sensitizers are unfavorable to DSSCs. Copyright
- Zhang, Zhiyun,Han, Jinlong,Li, Xin,Cai, Shengyun,Su, Jianhua
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supporting information
p. 2779 - 2785
(2013/08/23)
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- Modulation of spectrokinetic properties of o-quinonoid reactive intermediates by electronic factors: Time-resolved laser flash and steady-state photolysis investigations of photochromic 6- and 7-arylchromenes
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A ready synthetic accessibility of a series of 6- and 7-arylchromenes via Pd0-catalyzed Suzuki coupling protocol has permitted a comprehensive investigation of the thermal decay behavior of a broad set of photogenerated o-quinonoid reactive intermediates. It is shown that substantial mesomeric effect between the benzopyran nucleus and the aryl ring at C6 or C7 position of the former renders significant absorption beyond 350 nm such that they are readily photoactivated to yield colored o-quinonoid intermediates. The absorption spectra of the latter are found to be strongly influenced by the substituents on C2-, C6- and C7-aryl rings; indeed the colored absorptions can be conveniently tuned by appropriate choice of substituents. The thermal decay (bleaching phenomenon), which is important from the point of view of their application in ophthalmic lenses, was investigated in each case by μs-ms as well as real-time absorption spec-troscopy. By careful experimentation, we have extracted the decay rate constants for Z,E and E,E o-quinonoid isomers of all 6- and 7-arylchromenes in an attempt to establish a correlation between the electronic attributes with their thermokinetic behavior. From a combined analysis of μs-ms (laser flash) and real-time kinetic data, it is shown that the colored o-quinonoid intermediates decay faster when the C2-aryl and C6-/C7-aryl rings contain electron-donating and electron-accepting groups, respectively. In the same vein, the decay was found to occur slowly for the reversed scenario, while intermediate decay rates are observed when both substituents are electron-donating. Thus, any substituent on the C2-aryl ring that contributes mesomerically to the development of charge on the quinonoid oxygen, and any substituent on the C6-/C7-aryl ring that exerts -I effect appear to expedite thermal decay. Furthermore, evidence is obtained for the first time from μs time-resolved laser-flash spectroscopy for the formation and characterization of the trans,cis (E,Z) o-quinonoid isomer, which has heretofore eluded spectral characterization in the photochromic phenomena of pyrans.
- Moorthy, Jarugu Narasimha,Koner, Apurba L.,Samanta, Subhas,Roy, Ankur,Nau, Werner M.
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supporting information; experimental part
p. 4289 - 4300
(2009/12/07)
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- Polyaromatic amines. Part 3: Synthesis of poly(diarylamino)styrenes and related compounds
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The title compounds were synthesised and characterised as part of a study into new aromatic amines for charge transporting materials. Compounds 12-16, 20-24 and 27-34 are alkene linked triarylamines, compounds 35-36 are hydrazone derivatives and compounds 38-41 are pyrrole substituted triarylamines. Each compound was characterised by cyclic voltammetry.
- Plater, M. John,Jackson, Toby
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p. 4673 - 4685
(2007/10/03)
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- Inverse Triphenylmethylium Dyes
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When in the conventional triphenymethylium dye systems of the crystal violet and malachit green type, 6 and 7, the N-donor and C(+)-acceptor centers are interchanged, the "Inverse Triphenylmethylium Dye Types" 4 and 5 are obtained, showing very similar colors.The stable models with R = phenyl (8 - 10) and R = p-tolyl (11 - 13) were investigated in more detail.The visual observations were supported by the VIS spectra which showed nearly the same longest wavelength absorption maxima for corresponding pairs of inverse and conventional dye representatives.The experimental results can be interpreted with a simple HMO-model according to which the longest wavelength absorptions correspond here to transitions of equal energy from weakly bonding to nonbonding and from nonbonding to weakly antibonding molecular orbitals, respectively.On the same basis numerous isoelectronic variants of that dye type can be envisaged.In the NMR-spectra of the new dyes, characteristically increasing deshieldings of nearly all positions are observed in going from the mono- (10(+), 13(+)) through the di- (9(++), 12(++)) to the trications (8(+++), 11(+++)). - Key words: Dyes, Di-, Tricarbeniumions, NMR Spectra, VIS Spectra
- Hellwinkel, Dieter,Gaa, Heinrich Georg,Gottfried, Reiner
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p. 1045 - 1060
(2007/10/02)
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- Synthesis and Properties of N-Phenyl Derivatives of 4,4'-Diaminobenzophenone
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Variations in the reaction conditions during the Ullmann condensation of 4,4'-diaminobenzophenone with iodobenzene and the Goldberg diphenylamine synthesis with 4,4'-dibromobenzophenone and acetanilide or 4,4'-bis(acetamido)benzophenone and iodobenzene yielded the five possible partially and completely N-Phenylated 4,4'-diaminobenzophenones.By choice of starting materials, 4,4'-bis(phenylamino)benzophenone could be obtained in satisfactory yield.The infrared, ultraviolet, 1H and 13C nuclear magnetic resonance and mass spectra of the benzophenones are reported.
- Evans, Neil A.
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p. 409 - 413
(2007/10/02)
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