Synthesis, characterization, photophysical and electrochemical properties of a new non - planar perylene diimide with electron donating substituent

Date

2018-08-01

Author

Mostafanejad, S. Melika
Bodapati, Jagadeesh B.
Özkar, Saim
İCİL, Hüriye

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

132
views

0
downloads

A new nonplanar and soluble, donor-acceptor-donor system (3) based on a perylene diimide chromophore (1) consisting on 5-amino-4-cyano-3-methylthiophene-2-carboxamide (2) as electron donating unit at imide position has been synthesized. The photophysical and electrochemical properties were systematically investigated in different solvents. All the results of structural characterization reveal that the thiophene units are not coplanar with the core of perylene diimide. Spectroscopic properties of 3 in solution show variations with the organic solvent used. In the polar aprotic and strongly electron donating solvents, such as DMF, DMAC and NMP, 3 exhibits intense absorption features in the UV-visible absorption spectrum covering the wavelength range of 300-800 nm with excellent absorptivity. Photoinduced electronic excitation energy transfer was noticed in polar aprotic solvents from electron donating substituent to the perylene core. The non-planar geometry of 3 prevented efficient energy transfer between donor and acceptor.

Subject Keywords

Electrical and Electronic Engineering, General Computer Science, Atomic and Molecular Physics, and Optics, Electronic, Optical and Magnetic Materials

URI

https://hdl.handle.net/11511/34453

Journal

OPTICAL MATERIALS

DOI

https://doi.org/10.1016/j.optmat.2018.04.050

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis and characterization of a new soluble conducting polymer and its electrochromic devices Sahin, Elif; Sahmetlioglu, Ertugrul; Akhmedov, Idris M.; Tanyeli, Cihangir; Toppare, Levent Kamil (Elsevier BV, 2006-10-01) A new polythiophene derivative was synthesized by both chemical and electrochemical oxidative polymerization of 1-(perfluorophenyl)-2,5-di(2-thienyl)-1H-pyrrole (FPTPy). The structures of both the monomer and the soluble polymer were elucidated by nuclear magnetic resonance (H-1-NMR) and fourier transform infrared (FTIR). Polymer of FPTPy was also synthesized via potentiostatic electrochemical polymerization in acetonitrile (AN)/NaClO4/LiClO4 (0.1 M:0.1 M) Solvent-electrolyte couple. Characterizations of th...
Synthesis and characterization of conducting copolymers of succinic acid bis-(4-pyrrol-1-yl-phenyl) ester and their electrochromic properties Ertas, M; Çırpan, Ali; Toppare, Levent Kamil (Elsevier BV, 2004-05-07) A new dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and butanedioyl dichloride. Electrochemical behavior of this monomer, succinic acid bis-(4-pyrrol-1-yl-phenyl) ester (SM) was studied. Homopolymerization was achieved by chemical and constant Current electrolysis methods. Copolymerization of SM with thiophene was performed by constant potential electrolysis in acetonitrile (AN)-tetrabutylammonium tetrafluoroborate (TBAFB) and dichloromethane (DCM)-TBAFB, solvent-electroly...
Synthesis of a regular polymer containing pseudo-polyether cages Cihaner, A; Önal, Ahmet Muhtar (Elsevier BV, 2005-04-20) A new compound consisting of 2-thienyl units linked by polyether bridge has been synthesized and its electrochemical polymerization was performed via constant potential electrolysis (CPE) in an electrolytic solution containing 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF(6)) dissolved in CH3CN. Chemical polymerization was carried out using FeCl3 as oxidizing agent. It is found that both methods gave the same polymer product without any cleavage of the polyether bridge between thiophene (Th) rings. Al...
Synthesis and optical properties of fused aromatic thienopyrazine based pi-conjugated polymers Kolay, Merve; Tarkuc, Simge; Udum, Yasemin Arslan; Toppare, Levent Kamil (IOP Publishing, 2011-07-01) Two new polythieno[3,4-b]pyrazine derivatives, poly-10,12-bis(4-hexylthiophen-2-yl)dibenzo[f,h]thieno[3,4-b]quinoxaline (PDBTQ) and poly-8,10-bis(4-hexylthiophen-2-yl)acenaphtho[1,2-b]thieno[3,4-e]pyrazine (PATP) were synthesized by electrochemical polymerization and their electrochemical properties reported. Electroactivity of the monomer and electrochemical redox behavior of its polymers were investigated by cyclic voltammetry. Spectroelectrochemical analysis was performed and the band gaps of the polymer...
A new p- and n-dopable selenophene derivative and its electrochromic properties Cetin, Guelben Ardahan; Balan, Abidin; Durmus, Asuman; Günbaş, Emrullah Görkem; Toppare, Levent Kamil (Elsevier BV, 2009-02-01) A novel electrically conducting polymer, poly(2-dodecyl-4,7-di(selenophen-2-yl)benzotriazole) (PSBT), containing selenophene as the strong donor and benzotriazole as the strong acceptor groups was synthesized by electrochemical polymerization. Homopolymerization and copolymerization (in the presence of 3,4-ethylenedioxythiophene (EDOT)) were achieved in acetonitrile/dichloromethane(95/5 v/v) with 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF(6)). The electrochemical and optical properties of homopolym...

Citation Formats

S. M. Mostafanejad, J. B. Bodapati, S. Özkar, and H. İCİL, “Synthesis, characterization, photophysical and electrochemical properties of a new non - planar perylene diimide with electron donating substituent,” OPTICAL MATERIALS, pp. 30–38, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34453.