Synthesis of 2,2 '-[2,2 '-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)] tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics

Synthesis of 2,2 '-[2,2 '-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)] tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics Full article

Journal

Synthetic Metals
ISSN: 0379-6779

Output data

Year: 2019, Volume: 255, Article number : UNSP 116097, Pages count : DOI: 10.1016/j.synthmet.2019.06.013

Tags

Non-fullerene acceptors; pi-Extended TCNQ-based molecules; Functionalized anthra[2,3-b]thiophenes; Synthesis; Photovoltaic properties

Authors

Baranov Denis S. ^1,2 , Krivenko Olga L. ¹ , Kazantsev Maxim S. ^2,3 , Nevostruev Danil A. ¹ , Kobeleva Elena S. ^1,2 , Zinoviev Vladimir A. ⁴ , Dmitriev Alexey A. ^1,2 , Gritsan Nina P. ^1,2 , Kulik Leonid, V ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, VV Voevodsky Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
4	(Данные Web of science) Russian Acad Sci, Siberian Branch, AV Rzhanov Inst Semicond Phys, Novosibirsk 630090, Russia

Three novel molecules based on thiophene-fused 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) units linked through functionalized pi-conjugated arene bridges are synthesized by three-step sequence of Sonagashira coupling, double thioannulation and Knoevenagel condensation. The energy of their frontier orbitals shows that these molecules are suitable for replacing fullerenes as electron acceptors in composites with conjugated donor polymers used in organic photovoltaics (OPV). The composite of polymer donor PCDTBT with fluorene-linked thiophene-fused TCAQs demonstrates good solubility in organic solvents and bulk heterojunction morphology with characteristic donor and acceptor domain size of several tens of nanometers, favourable for photoelectric conversion. This composite also exhibits prominent light-induced EPR signal indicating efficient photoinduced free charge generation. OPV devices based on this composite were fabricated by vacuum-free method. They show photoelectric conversion with maximum PCE of 0.71%.

Baranov D.S. , Krivenko O.L. , Kazantsev M.S. , Nevostruev D.A. , Kobeleva E.S. , Zinoviev V.A. , Dmitriev A.A. , Gritsan N.P. , Kulik L.V.
Synthesis of 2,2 '-[2,2 '-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)] tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics
Synthetic Metals. 2019. V.255. UNSP 116097 . DOI: 10.1016/j.synthmet.2019.06.013 WOS Scopus РИНЦ OpenAlex

Published print:

Sep 1, 2019

Web of science:	WOS:000484648500001
Scopus:	2-s2.0-85067611919
Elibrary:	41701717
OpenAlex:	W2951282539

DB	Citing
Web of science	7
Scopus	7
Elibrary	4
OpenAlex	7