Dataset Information

Fluorinated Thieno[2',3':4,5]benzo[1,2-d][1,2,3]triazole: New Acceptor Unit To Construct Polymer Donors.

ABSTRACT: A new acceptor unit, fluorinated thieno[2',3':4,5]benzo[1,2-d][1,2,3]triazole (fBTAZT), has been designed and synthesized to build two donor-acceptor (D-A) copolymers with the none/fluorinated benzodithiophene (BDT) unit, which have been applied as the electron-donating material with ITIC as an electron-accepting material to fabricate the nonfullerene polymer solar cells (PSCs). It is found that fluorination at the BTAZT unit and BDT unit exerts a significant influence on photophysical properties and photovoltaic performances of the PSCs. As a result, when the fluorine atom is introduced both into the BTAZT unit and the side-chain thiophene ring of the BDT unit, the corresponding polymer PfBTAZT-fBDT exhibits deeper highest occupied molecular orbital-lowest unoccupied molecular orbital energy level and shows stronger interchain interaction with a little broad and red-shift absorption and high charge mobilities as well as good phase-separated morphologies, thus leading to higher power conversion efficiency of 6.59% in nonfullerene PSCs compared with another polymer PfBTAZT-BDT without F atom at the BDT unit, indicating that fBTAZT can be acted as a medium strong organic acceptor to build D-A polymer donor for high efficient PSCs.

SUBMITTER: Jiang X

PROVIDER: S-EPMC6645298 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Fluorinated Thieno[2',3':4,5]benzo[1,2-<i>d</i>][1,2,3]triazole: New Acceptor Unit To Construct Polymer Donors.

Jiang Xiu X Wang Jiacheng J Yang Yang Y Zhan Xiaowei X Chen Xingguo X

ACS omega 20181023 10

A new acceptor unit, fluorinated thieno[2',3':4,5]benzo[1,2-<i>d</i>][1,2,3]triazole (fBTAZT), has been designed and synthesized to build two donor-acceptor (D-A) copolymers with the none/fluorinated benzodithiophene (BDT) unit, which have been applied as the electron-donating material with ITIC as an electron-accepting material to fabricate the nonfullerene polymer solar cells (PSCs). It is found that fluorination at the BTAZT unit and BDT unit exerts a significant influence on photophysical pr ...[more]

PMID: 31458085

Similar Datasets

Project description:Benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) (isoBBT) is a new electron-withdrawing building block that can be used to obtain potentially interesting compounds for the synthesis of OLEDs and organic solar cells components. The electronic structure and delocalization in benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole), 4-bromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole), and 4,8-dibromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) were studied using X-ray diffraction analysis and ab initio calculations by EDDB and GIMIC methods and were compared to the corresponding properties of benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole (BBT). Calculations at a high level of theory showed that the electron affinity, which determines electron deficiency, of isoBBT was significantly smaller than that of BBT (1.09 vs. 1.90 eV). Incorporation of bromine atoms improves the electrical deficiency of bromobenzo-bis-thiadiazoles nearly without affecting aromaticity, which increases the reactivity of these compounds in aromatic nucleophilic substitution reactions and, on the other hand, does not reduce the ability to undergo cross-coupling reactions. 4-Bromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) is an attractive object for the synthesis of monosubstituted isoBBT compounds. The goal to find conditions for the selective substitution of hydrogen or bromine atoms at position 4 in order to obtain compounds containing a (het)aryl group in this position and to use the remaining unsubstituted hydrogen or bromine atoms to obtain unsymmetrically substituted isoBBT derivatives, potentially interesting compounds for organic photovoltaic components, was not set before. Nucleophilic aromatic and cross-coupling reactions, along with palladium-catalyzed C-H direct arylation reactions for 4-bromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole), were studied and selective conditions for the synthesis of monoarylated derivatives were found. The observed features of the structure and reactivity of isoBBT derivatives may be useful for building organic semiconductor-based devices.

Dataset Information

Fluorinated Thieno[2',3':4,5]benzo[1,2-d][1,2,3]triazole: New Acceptor Unit To Construct Polymer Donors.

Publications

Fluorinated Thieno[2',3':4,5]benzo[1,2-<i>d</i>][1,2,3]triazole: New Acceptor Unit To Construct Polymer Donors.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets