- Color-tunable organic composite nanoparticles based on perylene tetracarboxylic-diimides and a silicon-cored fluoranthene derivate
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Well-defined organic composite nanoparticles were prepared from perylene bisimide dye and silicon-cored fluoranthene derivate molecules. The composite nanoparticles exhibited good stability and thermal properties. The fluorescence emission of the perylene bisimide dye can be efficiently enhanced in composite nanoparticles based on efficient Foester resonant energy transfer. The composite nanoparticles exhibited tunable emission colors from blue to red by changing the concentration of the perylene bisimide dye. White-light emission with CIE coordinates (0.327, 0.339) was obtained as a good candidate for applications in white optoelectronic devices.
- Wang, Hua,Xie, Huanling,Liang, Yan,Feng, Linglong,Cheng, Xiyuan,Lu, Haifeng,Feng, Shengyu
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- 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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supporting information
p. 14720 - 14729
(2021/11/09)
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- Perylene diimide derivative as well as preparation method and application thereof (by machine translation)
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The perylene diimide derivative is named 1 - nitro - N, N - dicyclohexyl -3, 4:9, 10 - perylene diimide, the English name is 1-nitro-N, N-dicyclohexyl hexyl-3, 4:9, 10 - perylene diimide, and named PDI-NO. 2 , The derivative can be detected S a
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Paragraph 0032-0033
(2020/07/21)
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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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- Green and highly efficient synthesis of perylene and naphthalene bisimides in nothing but water
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High-purity, symmetrically substituted perylene and naphthalene bisimides were obtained by hydrothermal condensation of monoamines with the corresponding bisanhydride. The hydrothermal imidization proceeds quantitatively, without the need for organic solvents, catalysts or excess of the amines.
- Baumgartner, Bettina,Svirkova, Anastasiya,Bintinger, Johannes,Hametner, Christian,Marchetti-Deschmann, Martina,Unterlass, Miriam M.
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supporting information
p. 1229 - 1232
(2017/02/05)
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- Perylene imide with high dissolvability, and synthesis method thereof
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The invention discloses a perylene imide with high dissolvability, and a synthesis method thereof. The method comprises the following steps: synthesizing 1-p-formyl-N,N'-dicyclohexyl-3,4,9,10-perylene bisimide from 3,4,9,10-perylenetetracarboxylic dianhyd
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Paragraph 0045
(2017/09/01)
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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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- Self-assembled vesicle and rod-like aggregates of functionalized perylene diimide: Reaction-based near-IR intracellular fluorescent probe for selective detection of palladium
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Herein, we report design, synthesis, and self-assembly of perylene diimide (PDI) based near-IR intracellular probe (PS-PDI). PS-PDI molecules undergo aggregation to form self-assembled nanospheres and nanorods morphology in THF:H2O (1:1) and DM
- Singh, Prabhpreet,Mittal, Lalit Singh,Vanita, Vanita,Kumar, Kapil,Walia, Amandeep,Bhargava, Gaurav,Kumar, Subodh
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p. 3750 - 3759
(2016/06/09)
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- Templated Chromophore Assembly by Dynamic Covalent Bonds
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Through the simultaneous use of three orthogonal dynamic covalent reactions, namely disulfide, boronate, and acyl hydrazone formation, we conceived a facile and versatile protocol to spatially organize tailored chromophores, which absorb in the blue, red, and yellow regions, on a preprogrammed α-helix peptide. This approach allowed the assembly of the dyes in the desired ratio and spacing, as dictated by both the relative positioning and distribution of the recognition units on the peptide scaffold. Steady-state UV/Vis absorption and emission studies suggest an energy transfer from the yellow and red donors to the blue acceptor. A molecular dynamics simulation supports the experimental findings that the helical structure is maintained after the assembly and the three dyes are confined in defined conformational spaces.
- Rocard, Lou,Berezin, Andrey,De Leo, Federica,Bonifazi, Davide
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supporting information
p. 15739 - 15743
(2016/01/29)
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- Perylene diimide appended with 8-hydroxyquinoline for ratiometric detection of Cu2+ ions and metal displacement driven "turn on" cyanide sensing
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Perylene diimide (PDI) 3 and 4 appended with 8-hydroxyquinoline derivatives have been synthesized and their photophysical and spectroscopic properties have been experimentally determined. Moreover, PDIs 3 and 4 show ratiometric behavior to detect Cu2
- Singh, Prabhpreet,Mittal, Lalit Singh,Kumar, Sandeep,Bhargava, Gaurav,Kumar, Subodh
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p. 909 - 915
(2014/07/22)
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- 1,6- and 1,7-regioisomers of dinitro- and diamino-substituted perylene bisimides: Synthesis, photophysical and electrochemical properties
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1,6- and 1,7-regioisomers of dinitro- (1,6-3 and 1,7-3) and diamino-substituted perylene bisimides (1,6-1 and 1,7-1) were synthesized. The regioisomers 1,6-3 and 1,7-3 were successfully separated by high performance liquid chromatography and characterized
- Tsai, Hsing-Yang,Chang, Che-Wei,Chen, Kew-Yu
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p. 884 - 888
(2014/02/14)
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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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- 1,6-Dinitroperylene bisimide dyes: Synthesis, characterization and photophysical properties
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1,6- and 1,7-regioisomers of dinitro-substituted perylene bisimides (1a - 1b and 2a - 2b) were synthesized under mild condition in high yields. The 1,6- and 1,7-regioisomers were successfully isolated from the regioisomeric mixture using conventional meth
- Chang, Che-Wei,Tsai, Hsing-Yang,Chen, Kew-Yu
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p. 415 - 419
(2014/05/06)
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- 1,6- and 1,7-Regioisomers of asymmetric and symmetric Perylene Bisimides: Synthesis, characterization and optical properties
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The 1,6- and 1,7-regioisomers of dinitro- (1,6-A and 1,7-A) and diamino-substituted perylene bisimides (1,6-B and 1,7-B), and 1-Amino-6-nitro- and 1-Amino-7-nitroperylene bisimides (1,6-C and 1,7-C) were synthesized. The 1,6-A and 1,7-A regioisomers were
- Tsai, Hsing-Yang,Chang, Che-Wei,Chen, Kew-Yu
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p. 327 - 341
(2014/02/14)
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- 1,6- and 1,7-regioisomers of dinitro- and diamino-substituted perylene bisimides: Synthesis, photophysical and electrochemical properties
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1,6- and 1,7-regioisomers of dinitro- (1,6-3 and 1,7-3) and diamino-substituted perylene bisimides (1,6-1 and 1,7-1) were synthesized. The regioisomers 1,6-3 and 1,7-3 were successfully separated by high performance liquid chromatography and characterized
- Tsai, Hsing-Yang,Chang, Che-Wei,Chen, Kew-Yu
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p. 884 - 888
(2015/02/19)
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- Colorimetric and ratiometric fluorescent chemosensor for fluoride ion based on perylene diimide derivatives
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Based on a perylene diimide derivatives(PDIs) platform, AM-PDIs was rationally designed and synthesized as a new colorimetric and ratiometric fluorescent sensor for naked-eye detection of fluoride ion with high selectivity over other halide ions. Addition
- Chen, Zhi Jun,Wang, Li Min,Zou, Gang,Zhang, Liang,Zhang, Guan Jun,Cai, Xiao Fei,Teng, Ming Shuang
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experimental part
p. 410 - 415
(2012/06/01)
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- Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides
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1-Aminoperylene bisimides (1a-1c) were synthesized under mild condition in high yields, and were characterized by FT-IR, 1H NMR, UV-Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetric analyses. These
- Chen, Kew-Yu,Fang, Tzu-Chien,Chang, Ming-Jen
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scheme or table
p. 517 - 523
(2012/02/02)
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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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- 1,7-Dinitroperylene bisimides: Facile synthesis and characterization as n-type organic semiconductors
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1,7-Dinitroperylene bisimides (1a-1b) and 1-nitroperylene bisimides (2a-2b) were synthesized under mild condition in high yields, and were characterized by FT-IR, 1H NMR, UV-vis, HRMS spectra, cyclic voltammetry, and thermogravimetric analyses.
- Chen, Kew-Yu,Chow, Tahsin J.
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scheme or table
p. 5959 - 5963
(2010/11/21)
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- A "green" route to perylene dyes: Direct coupling reactions of 1,8-naphthalimide and related compounds under mild conditions using a "new" base complex reagent, t-BuOK/DBN
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The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed.
- Sakamoto,Pac
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- Very Soluble and Photostable Perylene Fluorescent Dyes
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The synthesis of perylene dyes 2 with two terminal alkyl groups is described.Long-chain alkyl groups do not increase, but diminish solubility.Cycloalkyl substituents give a minimum of solubility with medium sized rings and a maximum with the cyclotetradecyl derivative (2p).Very high solubility in organic solvents is attained by substitution with secondary alkyl residues having two long chains.One of them, the dye with the 1-hexylheptyl substituent (2v), exhibits a solubility of more than 100g/l in most solvents, a fluorescent quantum yield of about 100 percent, and a very high photostability, thus making it suitable for special applications.
- Demming, Stefan,Langhals, Heinz
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p. 225 - 230
(2007/10/02)
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- Soluble Perylene Fluorescent Dyes with High Photostability
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The preparation of several 3,4,9,10-perylenebis(dicarboximides) 1 is described and their photostability quantitatively determined and discussed.It is shown, that substitution of the insoluble perylene dye pigments with tert-butyl groups causes solubility in organic solvents leading to high quantum yields of these dyes.
- Rademacher, Andreas,Maerkle, Suse,Langhals, Heinz
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p. 2927 - 2934
(2007/10/02)
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