- Selective bromination of perylene diimides under mild conditions
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(Chemical Equation Presented) A novel method for the bromination of perylene diimides, PDI (1), under mild conditions is reported. Variation of the reaction conditions allows mono- and dibromination of PDIs to afford 2 and 3 (these can be separated throug
- Rajasingh, Paramasivan,Cohen, Revital,Shirman, Elijah,Shimon, Linda J. W.,Rybtchinski, Boris
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Read Online
- Preparation and characterization of regioisomerically pure 1,7-disubstituted perylene bisimide dyes
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A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respecti
- Wuerthner, Frank,Stepanenko, Vladimir,Chen, Zhijian,Saha-Moeller, Chantu R.,Kocher, Nikolaus,Stalke, Dietmar
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Read Online
- Tuning the aggregation behaviour of BN-coronene diimides with imide substituents and their performance in devices (OLEDs and OFETs)
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Compared to perylene diimides (PDIs), coronene diimides (CDIs), which can be viewed as a lateral core extension, show undesired effects for optoelectronic devices such as the decrease of the absorption and a hypsochromic shift. Here, we demonstrate that, if the core is extended with two BN units as opposed to two CC units, the opposite is true: large bathochromic shifts can be achieved, together with higher molar extinction coefficients and beneficial luminescence properties,e.g.small Stokes shifts and high quantum yields (Φlum> 94%). These effects can be explained by the influence of the BN-unit on the frontier molecular orbitals of theBNCDIs. Different substitution motifs at the imide position, cyclohexyl and 2,6-diisopropylphenyl, although they had no influence on the optical properties on a single molecule level, influenced the aggregation substantially so that the optical properties in the solid state and the performance in organic devices (OLEDs and OFETs) differed considerably. In combination with host matrices, devices with EQEs of up to 1.5% and white light emission (0.317; 0.346) were obtained. The developed synthetic route starting from a regioisomeric pure 1,7-substituted PDI leads toBNCDIs in good yields, which makes this class of compounds very promising.
- Geffroy, Bernard,Hissler, Muriel,Hoffmann, Jonas,Jaques, Emmanuel,Staubitz, Anne
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p. 14720 - 14729
(2021/11/09)
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- BN-Substituted coronene diimide donor-acceptor-donor triads: photophysical, (spectro)-electrochemical studies and Lewis behavior
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Boron/nitrogen substituted polyaromatic hydrocarbons (PAHs) are unique materials, with similar molecular structures to their carbon/carbon analogs, but different electronic properties. We report how these may be tuned by substitution at the B and/or N ato
- Hissler, Muriel,Hoffmann, Jonas,Jacquemin, Denis,Staubitz, Anne
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p. 13926 - 13934
(2021/10/20)
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- Modulating optical and electrochemical properties of perylene dyes by twisting aromatic π-system structures
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Three highly fluorescent perylene bisimide dyes were synthesized, where aromatic π-system structures are twisted to different degree by steric hindrance of two or four substitution groups at bay position. Light-emitting colours of these dye solutions can be modulated from green, yellow to red, and their fluorescence quantum yields increase up to approximate 100% with increasing the π-system twisting, which can be considered for new class of wavelength-tunable dye lasers. π-Twisted dyes are more sensitive to microenvironment changes. Thus, they are better fluorescence probe and sensory materials than planar dyes. Electrochemical cyclic voltammetry measurements revealed that these dyes are suitable for n-type optoelectrical devices and materials. These dye solids display near infra-red emission at 600–850 nm. Owing to strong π-π stacking interaction, planar dye solid loses its outstanding optical properties compared to its solution. In contrast, π-twisted dye solids retain their excellent optical properties including narrow emission bands and relatively high fluorescence quantum yields due to the suppression of π-π stacking interaction. Exceptional fluorescence polarization phenomena were observed for these π-twisted dye solids. These optical results revealed that π-twisted perylene bisimide dyes are more excellent optical materials than planar dyes.
- Wang, Ying,Zhang, Qi,Gong, Junbo,Zhang, Xin
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- Fluorescent probe PDI-CMA for continuously detecting Cu and dopamine as well as preparation method and application thereof
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The invention belongs to the field of fluorescent probes, and relates to preparation and application of a perylene bisimide fluorescent probe, in particular to a fluorescent probe for continuous detection of Cu and dopamine as well as a preparatio
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Page/Page column 0029; 0032; 0035
(2021/07/17)
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- Desymmetrization of Perylenediimide Bay Regions Using Selective Suzuki–Miyaura Reactions from Dinitro Substituted Derivatives
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Bay decoration of perylenediimide (PDI) is an attractive approach for tuning the optoelectronic properties of the dye as well as breaking backbone planarity, which provides the possibility of preventing the undesired formation of aggregates. This is usual
- Hruzd, Mariia,Rocard, Lou,Goujon, Antoine,Allain, Magali,Cauchy, Thomas,Hudhomme, Piétrick
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supporting information
p. 15881 - 15891
(2020/10/12)
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- Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes
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Practical synthesis of bay-monofunctionalized perylene dyes has been developed based on controllable NBS bromination of tetrabenzyl perylene-3,4,9,10-tetracarboxylate. The ability to perform the convenient and high-yielding synthesis highlights the potential utility of our multifunctional approach to access a diverse range of new perylene systems.
- Takahashi, Masaki,Asaba, Kyohei,Lua, Trinh Thi,Inuzuka, Toshiyasu,Uemura, Naohiro,Sakamoto, Masami,Sengoku, Tetsuya,Yoda, Hidemi
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supporting information
p. 624 - 631
(2018/01/27)
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- The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area
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The perylene diimide substituented by thiophene rings at bay area shows photoactivity and can be used as a photo sensor, but another one substituented by mestylene groups is photostable. The single crystal of 1,7-mesitylene perylene diimide was obtained. X-ray diffraction data of the crystal revealed that the plane of the perylene core was hardly twisted by introduction of mesitylene groups. These mestylene groups are like clips maintaining the planarity of the perylene core. Density functional theory calculation was applied to study the difference of photophysical and photochemical properties. The discovery is valuable for design guidance of perylene diimides.
- He, Junjie,Li, Song,Zeng, Heping
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p. 2800 - 2807
(2017/09/26)
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- Ionic Self-Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples
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The detection and quantification of spermine in clinical practice is important for early diagnosis of many diseases. Chromatographic and immunoassay-based methods are commonly used. However, a fluorescence-based assay could provide real-time detection. Herein, the synthesis and aggregation properties of a dicationic perylene probe (N1-dodecyl-N3-(4-phenyl)benzimidazolium-functionalized perylenediimide (DAB-PDI)) used to develop a fluorescent “turn-on” ensemble for the detection of spermine are discussed. The fluorescence of DAB-PDI (10 μm, Φ=0.55) is efficiently quenched by negatively charged sodium dodecylsulfate (SDS) through the formation of ionic self-assembled aggregates (charge ratio of negative (N) in SDS to positive (P) in DAB-PDI (N/P)=9). This negatively charged ionic self-assembly between DAB-PDI and SDS has been characterized by using photophysical, microscopic, dynamic light scattering, isothermal titration calorimetry, and HRMS techniques. The addition of spermine to this ensemble solution results in the breakdown of the DAB-PDI–SDS ensemble owing to strong binding of spermine with SDS and, as a result, the fluorescence of DAB-PDI is recovered. This ensemble exhibits high sensitivity and selectivity for spermine detection in water, urine, and blood serum. The lowest limit of detection is 27.5 nm, which is at least about 36 times lower than that required for early diagnosis of cancer (1 to 10 μm for urinary spermine).
- Singh, Prabhpreet,Mittal, Lalit Singh,Bhargava, Gaurav,Kumar, Subodh
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p. 890 - 899
(2017/04/24)
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- Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material
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The invention relates to a perylene diimide organic third-order nonlinear optical material. 3,4,9,10-perylenetetracarboxylic diimide serves as a core group; cyclohexane and benzanthrone or triphenylamine serve as substituent groups; cyclohexane is connected with an imide nitrogen atom of the core group; and benzanthrone or triphenylamine is connected with a bay of the core group to form a whole. A preparation method comprises the steps: (1) adding a perylene diimide derivative, a benzanthrone derivative or a triphenylamine derivative with the imide nitrogen atom connected with cyclohexane, and potassium carbonate into a solvent for dissolution, (2) after supplying nitrogen for 1-30 min, adding a tetrakispalladium catalyst, heating to 80-100 DEG C at a speed of 500-1200 r/min for reaction for 3-24h , (3) carrying out extraction, knockout and dryness for many times by using dichloromethane and distilled water, and (4) separating and purifying an obtained crude product. The perylene diimide organic third-order nonlinear optical material has a large nonlinear absorption coefficient and a two-photon absorption cross-section value and is applied to a third-order nonlinear optical material aspect.
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- Self-assembled nanorods of bay functionalized perylenediimide: Cu2+ based 'turn-on' response for INH, complementary NOR/OR and TRANSFER logic functions and fluorosolvatochromism
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We designed and synthesized the mono bay functionalized perylenediimide (PDI) derivative PDI-DMEA which undergoes self-assembly to form a nanorod morphology. The diameter of these nanorods is in the range of 150-300 nm and the length extended up to the μm range. These nanorods on interaction with Cu2+ ions transformed into spherical aggregates having a diameter of 350-600 nm in accordance with DLS studies. In solution, PDI-DMEA shows a blue shift of the internal charge transfer (ICT) absorption band from 605 to 570 nm along with a hyperchromic effect at 570 nm, in the presence of 0.7 equivalents of Cu2+ ions. The addition of 2 equivalents of Cu2+ ions results in complete disappearance of the ICT band at 570 nm and appearance of a normal absorption band of PDI at 515 nm (a visual colour change from colourless to yellow). On the other hand PDI-DMEA shows a strong fluorescence 'turn-on' response at 537 and 573 nm on addition of higher equivalents of Cu2+ ions. Thus, PDI-DMEA represents several examples of molecular switches such as 'OFF-ON-OFF' and 'ON-OFF-ON' at 570/515 nm (Cu2+, absorbance), and 'OFF-ON' at 570 nm (Fe2+, absorbance) and 537 nm (Cu2+, fluorescence) and thus offers the possibility for developing NOR, OR, INH and TRANSFER logic and complimentary logic circuits. Moreover, PDI-DMEA and the PDI-DMEA-Cu2+ complex show fluorosolvatochromism which helps to develop a colour array for differentiating organic solvents. The detailed mechanism of interaction of Cu2+ and Fe2+ with PDI-DMEA, confocal laser scanning microscopic studies, dynamic light scattering, 1H NMR titration and reversibility are discussed.
- Singh, Prabhpreet,Kumar, Kapil,Bhargava, Gaurav,Kumar, Subodh
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p. 2488 - 2497
(2016/07/14)
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- Graphene oxide/perylene bisimide donor-receptor composite material and preparation method
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The invention provides a graphene oxide/perylene bisimide donor-receptor composite material. A preparation method of the graphene oxide/perylene bisimide donor-receptor composite material is mainly characterized in that 3,4,9,10-perylenetetracarboxylic dianhydride is taken as a raw material, and a perylene bisimide derivative with low LOMO energy level and excellent photoelectric property is synthesized through bromination, amidation and nucleophilic substitution; then the graphene oxide/perylene bisimide organic-inorganic hybrid donor-receptor composite material is synthesized on the basis of nucleophilic substitution. The raw materials of the composite material are easy to obtain and low in cost, and the reaction yield is high. Graphene oxide has large specific surface area and contains oxygen-containing functional groups which can produce strong actions with metal ions, so that the composite material has high sensitivity and selective recognition on divalent copper metal ions in the environment and has pH sensitivity.
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- Regioisomerically pure 1,7-dibromo-substituted perylene bisimide dyes: Efficient synthesis, separation, and characterization
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1,7-Dibromo-substituted perylene bisimides have been obtained in yields of at least 60% in regioisomerically pure form by treating the commonly used dibromoperylene-3,4,9,10-tetracarboxylic dianhydride with 2-(diethylamino)ethylamine or 2-(dimethylamino)ethylamine and then separating the 1,7-isomer from the regioisomeric mixtures by conventional column chromatography and without recrystallization. The individual regioisomers were fully characterized by 1H NMR spectroscopy and HRMS. The signals of the protons located in the aromatic region and neighboring the imide nitrogen atom were utilized to confirm the chemical structures of the isomers. The 1,7-dibromo isomer obtained with 2-(dimethylamino)ethylamine in such a convenient and efficient way was further used to prepare 1,7-disubstituted perylene bisimide derivatives by saponification, amidation, and then bay-position substitution reactions. These compounds exhibited a significant redshift and broadening of their absorption and emission in optical spectroscopy analysis.
- Ma, Jiajun,Yin, Leicheng,Zou, Gang,Zhang, Qijin
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p. 3296 - 3302
(2015/05/20)
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- Light harvesting and amplification of emission of donor perylene-acceptor perylene aggregates in aqueous medium
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With the aid of rational design, we have synthesized a pair of water-soluble donor- and acceptor-type twisted perylene bisimide units, which together form aggregates upon lowering the pH of the medium, providing bright yellow fluorescence. The light-harvesting efficiency of the co-assembled system can be tuned by controlling the ratio of donor to acceptor and 98.1 % efficiency has been achieved. Light harvesting: Through the use of rational design, a pair of water-soluble donor- and acceptor-type twisted perylene bisimide units have been synthesized. Together, these form aggregates when the pH of the medium is lowered, emitting bright yellow fluorescence. The light-harvesting efficiency of the co-assembled system can be tuned by controlling the ratio of donor to acceptor and over 98 % efficiency has been achieved.
- Sukul, Pradip K.,Datta, Ayan,Malik, Sudip
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p. 3019 - 3022
(2014/03/21)
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- Structure-property relationships for 1,7-diphenoxy-perylene bisimides in solution and in the solid state
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To elucidate the impact of widely employed solubilizing phenoxy substituents on the structural and functional properties of perylene bisimide (PBI) dyes a series of 1,7-diphenoxy-substituted PBIs was prepared from 1,7-dibromo PBI which exhibit hydrogen, methyl, isopropyl or phenyl substituents at one or both ortho positions of the phenoxy substituents. Despite increasing sterical congestion high yields of 74-88% could be obtained for all twofold aromatic nucleophilic substitution reactions. The structural and optical properties in solution and in the solid state were investigated by 1H NMR, UV-Vis absorption and fluorescence spectroscopy, single crystal X-ray analyses (four structures) as well as quantum chemical and force field calculations. For the latter we used an adapted force field which correctly reflects the rigidity of the PBI core. Our studies show that these dyes prefer to accommodate a slightly twisted molecular structure in solution that is supported by CH...O hydrogen bonds between the 1,7-oxygen and the 6,12-hydrogen substituents. Because of the rather shallow potential energy surface, however, the molecules may planarize in the crystalline state under the influence of packing forces as revealed by single crystal X-ray analyses for two derivatives bearing methyl or phenyl substituents at all phenoxy ortho-positions. Such substituents are also suited to enwrap the PBI π-scaffold and to prohibit PBI aggregation in the bulk state giving rise to defined vibronic progressions in the solid state UV-Vis absorption and emission spectra, and appreciable fluorescence quantum yields of up to 37%. In dichloromethane solution all of these 1,7-diphenoxy-substituted PBI dyes exhibit fluorescence quantum yields of 98-100% despite significant differences in the shape of the UV-Vis absorption band. The latter was explained in terms of rigidity because the molecules bearing four ortho-substituents at the phenoxy substituents were shown to prevail in much more fixed conformations compared to their more simple counterparts. Our findings underline that the conformational flexibility of bay-substituents can have an important impact on the functional properties of PBI dyes.
- Jimenez, Angel J.,Lin, Mei-Jin,Burschka, Christian,Becker, Johannes,Settels, Volker,Engels, Bernd,Wuerthner, Frank
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p. 608 - 619
(2014/01/17)
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- Bay functionalized perylenediimide as a deaggregation based intracellular fluorescent probe for perchlorate
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The aggregates of perylenediimide based chemosensor (PDI 1) undergo de-aggregation induced fluorescence quenching selectively with ClO4-ions both in the solution and in the solid phase and can detect ClO4-ions in drinking water and fireworks. PDI 1 is permeable to C6 glioma cells, and ClO4-can be detected using confocal microscopy.
- Singh, Prabhpreet,Mittal, Lalit Singh,Vanita, Vanita,Kumar, Rahul,Bhargava, Gaurav,Walia, Amandeep,Kumar, Subodh
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p. 13994 - 13997
(2015/11/17)
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- Synthesis and characterization of perylene diimide based molecular multilayers using CuAAC: Towards panchromatic assemblies
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Three perylene diimides (PDI) were synthesized with propargyl groups at the diimide positions to enable the fabrication of molecular multilayer thin films via sequential copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) coupling reactions in a layer-by-layer (LbL) fashion. The new PDIs with phenoxy (PhO-PDI), dodecylthiol (Thiol-PDI), and pyrrolidine (Pyrr-PDI) substituents in bay positions have optical absorption spectra that span a large portion of the visible region. Multilayer growth on 11-azidoundecylsiloxane coated silica glass and indium tin oxide (ITO) surfaces was demonstrated up to 10 bilayers of each PDI with 1,3,5-tris(azidomethyl)-benzene (N3Mest) via optical and infrared spectroscopy. Polarized UV-visible absorption measurements showed a strong dependence on the orientation of the film in the light path and was consistent with a preferential orientation of the PDI molecules in the film at 40-42° with respect to the substrate surface. Grazing-angle attenuated total reflectance (GATR) infrared spectra of the films show an increase in content of unreacted azides during multilayer growth from N3Mest as a result of the smaller molecular footprint as compared to the PDI components. Electrochemical scans of the multilayer films grown on ITO exhibited reversible two-electron reduction waves for the PDIs with linear increases in charge with bilayer growth. The electrochemically derived surface coverages of PDIs averaged 1.2-1.3 × 1014 molecules per cm2 for each layer added to the multilayer films. The flexibility of the CuAAC based LbL assembly methodology is highlighted by the assembly of a mixed multilayer film containing five layers of each PDI, resulting in a panchromatic film that is a summation of individual chromophores. This journal is the Partner Organisations 2014.
- Beauvilliers, Evan E.,Topka, Michael R.,Dinolfo, Peter H.
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p. 32866 - 32875
(2014/08/18)
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- 1,7-Diaminoperylene bisimides: Synthesis, optical and electrochemical properties
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A series of blue dyes, 1,7-diaminoperylene bisimides (2a-2c), was synthesized under mild condition in high yields, and was characterized by 1H NMR, UV-Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetr
- Tsai, Hsing-Yang,Chen, Kew-Yu
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p. 319 - 327
(2013/02/22)
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- Facile synthesis of 1-bromo-7-alkoxyl perylene diimide dyes: Toward unsymmetrical functionalizations at the 1,7-positions
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In this Letter, we report a facile approach to synthesize unsymmetrical 1-bromo-7-alkoxyl perylene diimides by the nucleophilic substitution of one of the two 1,7-dibromo units with an alkyl alcohol using K2CO 3 as the base. A furthe
- Zhang, Xin,Pang, Shufeng,Zhang, Zhigang,Ding, Xunlei,Zhang, Shanlin,He, Shenggui,Zhan, Chuanlang
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supporting information; experimental part
p. 1094 - 1097
(2012/03/26)
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- Tetraphenylethenyl-modified perylene bisimide: Aggregation-induced red emission, electrochemical properties and ordered microstructures
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Perylene bisimides (PBIs) are one class of the most explored organic fluorescent materials due to their high fluorescence quantum efficiency, electron transport behaviour, and ready to form well-tailored supramolecular structures. However, they suffer from heavy aggregation-caused quenching (ACQ) effect which has greatly limited their potential applications. We successfully tackle this problem by chemical modification of the PBI core with two tetraphenylethene (TPE) moieties at the bay positions. This modification resulted in a pronounced fluorescence red-shift (over 120 nm) and rendered the derivatives (1,6-/1,7-DTPEPBI) with evident aggregation-induced emission (AIE) behaviour. Both 1,6-DTPEPBI and 1,7-DTPEPBI emit bright red fluorescence in the solid state. The fluorescence quantum efficiency of the aggregates of 1,7-DTPEPBI (ΦF, solid = 29.7%, formed in a hexane/ dichloromethane mixture, fh = 90%) is about 424 times higher than that in dichloromethane solution (ΦF, solut = 0.07%). Electrochemical investigation results indicated that 1,7-DTPEPBI sustained the intrinsic n-type semiconductivity of PBI moiety. In addition, morphological inspection demonstrated that 1,7-DTPEPBI molecules easily form well-organized microstructures despite the linkage of the PBI core with bulky TPE moieties.
- Zhao, Qiuli,Zhang, Shuang,Liu, Yi,Mei, Ju,Chen, Sijie,Lu, Ping,Qin, Anjun,Ma, Yuguang,Sun, Jing Zhi,Tang, Ben Zhong
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p. 7387 - 7394
(2012/06/01)
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- Synthesis and characterization of a new perylene bisimide (PBI) derivative and its application as electron acceptor for bulk heterojunction polymer solar cells
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A symmetrical perylene bisimide derivative (PBI) with 2-(4-nitrophenyl) acrylonitrile groups at the 1,7 bay positions of perylene and solubilizing cyclohexyl units was synthesized and characterized. The absorption spectrum of PBI was broad with the most prominent peak at 655 nm and optical band gap of 1.72 eV. The electrochemical investigation indicates that PBI has a LUMO energy level of -3.9 eV which is similar to that of PCBM or PC70BM. Bulk heterojunction solar cell fabricated using a blend of poly(3-hexylthiophene) (P3HT) and PBI (1:1 w/w) as active layer cast from THF exhibited power conversion efficiency (PCE) at 1.56%. However, the device with P3HT:PBI blend deposited from mixed solvent (DIO/THF) improved the PCE to 2.78% which further increased to 3.17% on using the thermal annealed active layer. The improvement in the PCE is attributed to the enhanced crystallinity of the blend (particularly P3HT) and increase in hole mobility leading to balanced charge transport.
- Sharma,Roy,Mikroyannidis,Justin Thomas
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p. 3118 - 3129
(2013/02/22)
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- Method for producing organic field-effect transistors
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A method for producing an organic field-effect transistor, comprising the steps of: a) providing a substrate comprising a gate structure, a source electrode and a drain electrode located on the substrate, andb) applying an n-type organic semiconducting compound to the area of the substrate where the gate structure, the source electrode and the drain electrode are located, wherein the n-type organic semiconducting compound is selected from the group consisting of compounds of the formula I wherein R1, R2, R3and R4are independently hydrogen, chlorine or bromine, with the proviso that at least one of these radicals is not hydrogen,Y1 is O or NRa, wherein Ra is hydrogen or an organyl residue,Y2 is O or NRb, wherein Rb is hydrogen or an organyl residue,Z1, Z2, Z3 and Z4 are O, where, in the case that Y1 is NRa, one of the residues Z1 and Z2 may be a NRc group, where Ra and Rc together are a bridging group having 2 to 5 atoms between the terminal bonds, where, in the case that Y2 is NRb, one of the residues Z3 and Z4 may be a NRd group, where Rb and Rd together are a bridging group having 2 to 5 atoms between the terminal bonds.
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Page/Page column 36
(2011/04/18)
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- Synthesis and characterization of 1,7-disubstituted and 1,6,7,12-tetrasubstituted perylenetetracarboxy-3,4:9,10-diimide derivatives
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A variety of perylenetetracarboxy-3,4:9,10-diimide derivatives have been synthesized. Particular attention was paid to substituents in positions 1, 6, 7 or 12. The energy differences between the frontier orbitals have been determined using optical spectroscopy (UV and fluorescence). The energy of the lowest unoccupied orbitals (LUMOs) were obtained by cyclic voltammetry. From both studies, the energies of the highest occupied orbitals (HOMOs) were also been calculated. A Hammett-type relationship was observed for the reduction potentials (Ered11/2) when correlated with the σ-ortho parameter. The energies of the frontier orbitals define the domains of application of these compounds. They significantly depend on the substitution in positions 1, 6, 7, or 12.
- Queste, Mathieu,Cadiou, Cyril,Pagoaga, Bernard,Giraudet, Louis,Hoffmann, Norbert
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experimental part
p. 2537 - 2545
(2011/01/12)
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- Synthesis and photovoltaic properties of novel alternating phenylenevinylene or fluorenevinylene copolymers containing perylene bisimide
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Two novel alternating phenylenevinylene copolymers P6 and P12 as well as one fluorenevinylene copolymer F connected at the 1,7 bay positions with perylene bisimide were synthesized by Heck coupling. They were characterized by GPC, FT-IR, 1H NMR, TGA, TMA, UV-vis, cyclic voltammetry and photoluminescence (PL) emission spectra. The copolymers were soluble in common organic solvents and thermally stable up to ~300 °C. Their glass transition temperatures were 48-60 °C. The long wavelength absorption maximum was located at 510-542 nm with optical band gaps of ~2.0 eV. The PL emission maximum of P6 and P12 was red-shifted relative to F. The photovoltaic performance of P6, P12 and F was also investigated.
- Mikroyannidis, John A.,Cheung, Kai Yin,Fung, Man Kin,Djuri?i?, Aleksandra B.
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scheme or table
p. 426 - 432
(2011/12/03)
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- POLYCYCLIC ORGANIC COMPOUNDS, RETARDATION LAYER AND COMPENSATION PANEL ON THEIR BASE
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This invention relates to polycyclic organic compounds of general structural formula (I): wherein Y is a predominantly planar polycyclic system being at least partially aromatic, W1, W2, and W3 are different groups providing solubility in an organic solvent, and sum (n1 +n2+n3) is 1, 2, 3, 4, 5, 6, 7 or 8. The polycyclic organic compounds are substantially transparent for electromagnetic radiation in the visible spectral range and are capable of forming supramolecules in the organic solvent.
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Page/Page column 12-13
(2009/10/22)
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- POLYCYCLIC ORGANIC COMPOUNDS, POLARIZING ELEMENTS AND METHOD OF PRODUCTION THEREOF
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This invention relates to polycyclic organic compounds of a general structural formula (I): wherein Y is a predominantly planar polycyclic system being at least partially aromatic, W1, W2, and W3 are different groups providing solubility in an organic solvent, and sum n1 +n2+n3 is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, which are capable of forming supramolecular structures in a wide range of organic solvents, and which are capable of absorbing electromagnetic radiation in at least one subrange of the visible spectral range.
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Page/Page column 18-19
(2009/10/22)
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- Rigid oligoperylenediimide rods: Anion-π slides with photosynthetic activity
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(Chemical Equation Presented) Slide rules: A new class of membrane-active rigid-rod molecules comprising π-acidic, n-semiconducting oligoperylene-diimides is introduced (see picture). They are able to combine passive anion transport across lipid bilayers with photoactive electron transport in the other direction across intact vesicle membranes. Thus, the compounds demonstrate artificial photosynthetic activity.
- Perez-Velasco, Alejandro,Gorteau, Virginie,Matile, Stefan
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p. 921 - 923
(2008/09/20)
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- 1,6-Disubstituted perylene bisimides: Concise synthesis and characterization as near-infrared fluorescent dyes
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Detailed studies on bromination and subsequent imidization of perylene bisanhydride were reported. 1,6,7,12-Tetrabromoperylene bisimide was obtained in an optimized high yield. In addition, 1,6-disubstituted regioisomer was separated for the first time in isomerically pure form, and the structure was confirmed by 1H NMR, MS, element analysis, and photophysical measurements. By using a mixture of regioisomers 1,6- and 1,7-dibromo-perylene bisimide, 1,6-dipiperidinylperylene bisimides (1,6-Piper-Pery) were synthesized, purified, and their fluorescence were measured with a peak at 760 nm. These compounds can be used as stable near-infrared absorbing and fluorescent dyes.
- Fan, Liqiang,Xu, Yanping,Tian, He
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p. 4443 - 4447
(2007/10/03)
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- High-mobility air-stable n-type semiconductors with processing versatility: Dicyanoperylene-3,4:9,10-bis(dicarboximides)
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Taking up the semiconducting baton: Organic field-effect transistors fabricated with a new class of extremely electron-deficient cyanated perylene diimides are air-stable and exhibit n-type mobilities as high as 0.64 cm 2V-1 s-1 (see scheme). Devices can be fabricated from vapor-deposited and solution-cast films as well as top- and bottom-contact electrode configurations. (Graph presented).
- Jones, Brooks A.,Ahrens, Michael J.,Yoon, Myung-Han,Facchetti, Antonio,Marks, Tobin J.,Wasielewski, Michael R.
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p. 6363 - 6366
(2007/10/03)
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