Structural, photophysical and optoelectronic activity of triphenylamine-based push-pull chromophores: a theoretical study

Date

2022-12-01

Author

Yahya, Mohamed
Suvitha, A.
Bouzıanı, Asmae

Metadata

Show full item record

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

Item Usage Stats

138
views

0
downloads

Triphenylamine was used as a donor and electron-withdrawing groups in different positions as terminal acceptor groups in order to design a series of push-pull chromophores (D1-5). The dyes were characterized via UV-vis spectroscopy and electric, absorption, and thermal studies. Based on the theoretical results, the electrochemical and optical investigations of D1-5 displayed reduced bandgap HOMO-LUMO energies. In addition, these compounds exhibited an electrical character, making them promising donor dyes for solar cell usage. The B3LYP/6-31G (d, p) basis set using the density functional theory (DFT) was applied in this study. The second-order NLO response was also investigated for D1-5 chromophores. D1-5 compounds have higher second-order nonlinear characteristics and a smaller HOMO-LUMO gap than electron-accepting groups ranging from ultraviolet to near-infrared. The thermodynamic properties were also calculated as a function of temperature in the 298.15 K range, including heat capacity, entropy, enthalpy, free energy, and zero-point energy.

Subject Keywords

Triphenylamine-based push-pull chromophores, FMO, NLO, MEP, Chemical reactivity, NONLINEAR-OPTICAL CHROMOPHORES, ELECTROOPTIC ACTIVITY, SYSTEMS, BRIDGE, DYES, NLO

URI

https://hdl.handle.net/11511/100841

Journal

OPTICAL AND QUANTUM ELECTRONICS

DOI

https://doi.org/10.1007/s11082-022-04239-w

Collections

Department of Chemical Engineering, Article

Suggestions

OpenMETU
Core

Structure-property relationships: Influence of number of anchoring groups in triphenylamine-carbazole motifs on light harvesting and photovoltaic performance for dye-sensitized solar cells Elsherbiny, Dalia; Yıldırım, Erol; El-Essawy, Farag; Abdel-Megied, Ahmed; El-Shafei, Ahmed (2017-12-01) Three novel organic sensitizers were molecularly designed and synthesized based on triphenylamine (TPA), as the core donor (D-TPA), linked to one, two or three carbazole (D-Carb) moieties with different number of anchoring groups (AG) to generate: D-TPA-pi-D-carb-A (DE1), D-TPA(pi-D-Carb-A)(2) (DE-2) and D-TPA(pi-D-Carb-A)(3) (DE-3). The primary goal of this study was to investigate the influence of bridging different number of Dcarb and AG, through it -spacer, with TPA on the photovoltaic performance in DS...
Syntheses and Optical Properties of Perfluorophenyl Containing Benzimidazole Derivatives: The Effect of Donor Units ILERI, Merve; HACIOGLU, Serife O.; Çırpan, Ali; Toppare, Levent Kamil (2015-07-03) Synthesis of two novel donor - acceptor - donor type monomers containing benzimidazole as the acceptor unit and thiophene and 3,4-ethylenedioxythiophene (EDOT) as the donor units were performed. 2-(Perfluorophenyl)-4,7-di(thiophen-2-yl)-1H-benzo[d]imidazole and 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-(perfluorophenyl)-1H-benzo[d]imidazole were synthesized successfully and polymerized electrochemically. The electrochemical and spectroelectrochemical studies of the polymers were studied. The effec...
Push-pull chromophores by reaction of 2,3,5,6-tetrahalo-1,4-benzoquinones with 4-(N,N-dialkylanilino)acetylenes Dengiz, Çağatay; GAWEL, Przemyslaw; TRAPP, Nils; RUHLMANN, Laurent; BOUDON, Corinne; DIEDERICH, Francois (2016-03-03) A series of new push-pull chromophores were synthesized from electron-rich 4-(N,N-dialkylanilino) acetylenes and 2,3,5,6-tetrahalo-1,4-benzoquinones. The reactivity of the latter differs substantially from that of the previously investigated 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The transformation with fluoranil gave orange-colored, bis-donor-substituted chromophores with a tricyclic, cyclobutene-fused dihydrobenzofuranone core. In contrast, the reaction with chioranil yielded mono donor-substitu...
Synthesis and electrochemical polymerization of D-A-D type monomers with thieno [3,4-c] pyrrole-4,6-dione acceptor unit Çakal, Deniz; Cihaner, Atilla; Önal, Ahmet Muhtar (Elsevier BV, 2018-11-01) In this study, three new donor-acceptor-donor type monomers bearing 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno [3,4-c]pyrrole- 4,6(5H)-dione (A) as an acceptor unit and thiophene, 3,4-ethylenedioxythiophene (EDOT) and 3,3-didecy1-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (didecyl-ProDOT) as donor units were synthesized via Stille cross-coupling reaction and their electrochemical polymerization by repetitive cycling was reported. The electrochemical and optical properties of the monomers ((5-(2-ethyl-liexyl)-1,...
Synthesis and electrochemical characterization of fluorene and benzimidazole containing novel conjugated polymers: Effect of alkyl chain length on electrochemical properties Namal, Imge; Ozelcaglayan, Ali Can; Udum, Yasemin Arslan; Toppare, Levent Kamil (Elsevier BV, 2013-10-01) The synthesis and characterization of two donor acceptor type conjugated polymers were investigated. Electrochemical properties were examined by cyclic voltammetry, spectroelectrochemistry and kinetic studies. The increase in the alkyl chain length attached to the fluorene unit was investigated in terms of electrochemical properties. The synthesis was carried out via Stille coupling of 4,7-dibromo-4'-(tert-butyl)spiro[benzo[d]imidazole-2,1' cyclohexane] and 2,5-bis(tributylstannyl)thiophene with 9,9-dihexyl...

Citation Formats

M. Yahya, A. Suvitha, and A. Bouzıanı, “Structural, photophysical and optoelectronic activity of triphenylamine-based push-pull chromophores: a theoretical study,” OPTICAL AND QUANTUM ELECTRONICS, vol. 54, no. 12, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: https://hdl.handle.net/11511/100841.