- Synthesis and properties of a tetrathiafulvalene-perylene tetracarboxylic diimide-tetrathiafulvalene dyad
-
A donor-acceptor-donor dyad 4 involving 2-sulfur-3-methylthio-6,7- bis(hexylthio)tetrathiafulvalene (TTF) as a donor attached directly to N,N′-dibutylperylene-3,4,9,10-tetracarboxylic diimide (PDI) as an acceptor was synthesized by condensation of N,N′-dibutyl-1,6-dibromo-3,4,9,10- perylenetetracarboxylic diimide and 2-(2-cyanoethylthio-3-methylthio-6,7- bis(hexylthio)tetrathiafulvalene. The cyclic voltammetric (CV) data implied significant intramolecular interaction and the absorption spectrum indicated that there was an intramolecular charge transfer (ICT) interaction between TTF and PDI moieties in dyad 4. Comparing with PDI 13, the fluorescence emission intensity of dyad 4 was quenched almost quantitatively, which might result from the photo-induced electron transfer (PET) interaction between the PDI and TTF moieties in dyad 4. The fluorescence intensity of dyad 4 could be reversibly modulated by sequential oxidation and reduction of the TTF unit using chemical methods. Thus dyad 4 can be regarded as a new reversible fluorescence-redox dependent molecular switch. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.
- Zhang, Yu,Cai, Liang-Zhen,Wang, Cheng-Yun,Lai, Guo-Qiao,Shen, Yong-Jia
-
-
Read Online
- Design, photochemistry and antibacterial evaluation of novel light-harvesting antenna
-
Novel light-harvesting compound 6, based on 1,8-naphthalimide donors and perylenediimide acceptor were synthesized. The light-harvesting compound 6 showed intensive absorption band in range between 390 and 560 nm, that is 50 nm wider in comparison with the absorption of the model perylene dye. The novel antenna 6 has a higher ability to collect photons from environment in comparison with the single perylene diimide dyes. The chosen fluorophore units are suitable donor–acceptor pair for light-harvesting materials which was in agreement with their good antibacterial activity.
- Bojinov, Vladimir B.,Georgiev, Nikolai I.,Sakr, Alaa R.
-
-
Read Online
- Practical Preparation of Octa- and Tetrabromoperylene Diimides and Derivatives Thereof
-
A mild synthesis of fully brominated perylene dianhydride and diimides in one step from easily available unsubstituted precursors is presented. The partial reduction of ortho -bromo substituents with hydrazine hydrate allowed for a gram-scale synthesis of a valuable intermediate, 1,6,7,12-tetrabromoperylene diimide. Several new twisted fully core-substituted perylene diimide derivatives having sulfur, nitrogen, or oxygen substituents were synthesized using regioselective nucleophilic substitution reactions.
- Jozeliunaite, Augustina,Striela, Romualdas,Labanauskas, Linas,Orentas, Edvinas
-
-
Read Online
- Luminescent one-dimensional nanostructures of perylene bisimides
-
(Chemical Equation Presented) Perylene bisimides form a unique class of organic semiconductors, in this investigation two symmetrical perylene bisimides caped with 1-butyl (B-PTCDI) and 4,4-diethoxybutyl (DB-PTCDI) have been synthesized and characterized. The compounds self-assembled as a network of nanobelts and nanorods in the solution based self-assembly process. Morphologies of these self-assembled structures were characterized by optical, fluorescence, scanning and transmission electronic microscopic techniques. One-dimensional self-assemblies of B-PTCDI and DB-PTCDI molecules are due to the strong π-π stacking ability of perylene core and assistance given by the side chains and solvent. Observed molecular self-assembly and electronic properties of the molecules. The observed self-assembly was supported by molecular modeling studies using density functional theory.
- Boobalan,Imran,Nagarajan
-
-
Read Online
- Core Perylene Diimide Designs via Direct Bay- and ortho-(Poly)trifluoromethylation: Synthesis, Isolation, X-ray Structures, Optical and Electronic Properties
-
We developed an efficient solvent- and catalyst-free direct polytrifluoromethylation of solid perylene-3,4,9,10-tetracarboxylic dianhydride that produced a new family of (poly)perfluoroalkyl bay- and ortho-substituted PDIs with two different imide substituents. Direct hydrogen substitution with CN group led to the synthesis of a cyanated perfluoroalkyl PDI derivative for the first time. Absorption, steady-state and time-resolved emission, X-ray diffraction, electrochemical, and gas-phase electron affinity data allowed for systematic studies of substitution effects at bay, ortho, and imide positions in the new PDIs. Solid-state packing showed remarkable variations in the intermolecular interactions that are important for charge transport and photophysical properties. Analysis of the electrochemical data for 143 electron poor PDIs, including newly reported compounds, revealed some general trends and peculiar effects from substituting electron-withdrawing groups at all three positions.
- Clikeman, Tyler T.,Bukovsky, Eric V.,Wang, Xue-Bin,Chen, Yu-Sheng,Rumbles, Garry,Strauss, Steven H.,Boltalina, Olga V.
-
-
Read Online
- Visible-light photocatalytic aerobic oxidation of sulfides to sulfoxides with a perylene diimide photocatalyst
-
Photosensitized oxygenation has been recognised as a modern method of incorporating oxygen into a substrate, as it offers environmentally benign alternatives to several conventional synthetic procedures. A metal-free aerobic selective sulfoxidation photos
- Gao, Yueying,Xu, Huan,Zhang, Shiwei,Zhang, Yan,Tang, Chunlei,Fan, Weizheng
-
supporting information
p. 7144 - 7149
(2019/08/07)
-
- Method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing
-
The invention discloses a method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing. The method is characterized in that multi-halogenated perylenediimide arene is effectively subjected to dehalogenation reduction by one step in the presence of an organic solvent through an inert atmosphere reactor under a catalyzing system containing dibromo cobalt with a catalyzing quantity, excessive manganese powder and excessive sodium formate. According to the method, the synthesizing route has the advantages of being simple, efficient, low in price of raw materials, low in synthesizing cost, and high in repeatability and can be widely applied to dehalogenation reduction reaction of other halogenated aromatic hydrocarbons.
- -
-
Paragraph 0031-0032; 0036; 0037
(2018/09/28)
-
- Organic field-effect transistors based on disubstituted perylene diimides: Effect of alkyl chains on the device performance
-
The preparation and systematic investigation of n-type semiconductor materials based on disubstituted perylene diimides (PDIs) possessing alkyl chains with variable length (from C4 to C12) are reported. It was shown that electrical characteristics of field-effect transistors can be tuned by changing the length of the alkyl chains in the PDIs used as semiconductor materials.
- Mumyatov, Alexander V.,Leshanskaya, Lidiya I.,Anokhin, Denis V.,Dremova, Nadezhda N.,Troshin, Pavel A.
-
p. 306 - 307
(2015/02/02)
-
- Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides
-
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
-
scheme or table
p. 517 - 523
(2012/02/02)
-
- WRITABLE AND ERASABLE HIGH-DENSITY OPTICAL STORAGE MEDIA
-
The invention relates to an optical storage medium comprising a substrate and a storage layer, wherein the storage layer comprises a compound of the formula (I) or (II)in which A and A', independently of one another, are unsubstituted or mono- or di-halo-, -hydroxy-, -C1-C6alkyl-, -C1-C6alkoxy-, -cyano- or -nitro-substituted phenyl, pyridyl, pyrrolyl, imidazolyl, furyl or thienyl, which can, if desired, be fused to a benzene ring, are halide, tetrafluoroborate or unsubstituted or with one or more halogen substituted C1-C6alkane-sulfonate, benzenesulfonate, C1-C6alkylbenzenesulfonate, C1-C6alkylsulfate or di-C1-C6alkyl-phosphonate of N-C1-C6alkyl-pyridiniumyl, or are unsubstituted or mono- or di-hydroxy-substituted C2-C6alkyl or C2-C6alkenyl, whose chain may be uninterrupted or interrupted by one or two oxygen atoms, B and B', independently of one another, are 2 H, S, S2 or SO2, and n and n', independently of one another, are each a number from 1 to 4. The invention also relates to a process for the optical writing, storage, reading, modification or erasing of data at a wavelength of from 400 to 700 nm using a novel recording medium, to an optical recorder for the optical writing, modification or erasing of data using only continuous laser radiation or only modulated laser radiation, to a process for converting a compound of the formula (I) or (II) from a black form into a red form by mechanical force, and to new compounds of the formula (I) or (II).
- -
-
Page/Page column 11-12
(2008/06/13)
-
- Intramolecular energy transfer in a tetra-coumarin perylene system: Influence of solvent and bridging unit on electronic properties
-
The synthesis and characterisation of a novel coumarin donor-perylene bisimide acceptor light-harvesting system is reported, in which an energy-transfer efficiency of >99% is achieved. Comparison of the excited-state properties of the donor-acceptor syste
- Hurenkamp, Johannes H.,Browne, Wesley R.,Augulis, Ramnas,Puglys, Audrius,Van Loosdrecht, Paul H. M.,Van Esch, Jan H.,Feringa, Ben L.
-
p. 3354 - 3362
(2008/10/09)
-
- The Relation between Packing Effects and Solid State Fluorescence of Dyes
-
The solid state fluorescence of diketopyrrolopyrrole dyes and perylene-3,4:9,10-tetracarboxylic bisimides with alkyl substituents are investigated and compared with noncovalent interactions.The latter are estimated by crystal structure analysis, heats and entropies of fusion and solubilities in organic solvents.Applications of the dyes are discussed.
- Langhals, H.,Demmig, St.,Potrawa, Th.
-
p. 733 - 748
(2007/10/02)
-