Influence of the Location of Electron-Donating 3,4-Ethylenedioxythiophene (EDOT) Moiety in the A–π–D–π–A Type Conjugated Molecules on the Optoelectronic Properties and Photovoltaic Performances

Lilei Wang; Ying Zhang; Xiang Guan; Wei Gao; Yi Lin; Qun Luo; Hongwei Tan; Hai-Bo Yang; Chang-Qi Ma

doi:10.1055/a-1472-7109

Organic Materials, Table of Contents

CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 204-213
DOI: 10.1055/a-1472-7109

Focus Issue: Peter Bäuerle 65th Birthday

Original Article

Influence of the Location of Electron-Donating 3,4-Ethylenedioxythiophene (EDOT) Moiety in the A–π–D–π–A Type Conjugated Molecules on the Optoelectronic Properties and Photovoltaic Performances

Lilei Wang

^aPrintable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China

^bDepartment of Chemistry, Shanghai Key Laboratory of Green Chemistry and Chemical, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China

,

Ying Zhang

^cCollege of Chemistry, Beijing Normal University, 19 XinJieKouWai Street, HaiDian District Beijing 100875, P. R. China

,

Xiang Guan

^aPrintable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China

,

Wei Gao

^aPrintable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China

,

Yi Lin

^dDepartment of Chemistry, Xi'an Jiaotong Liverpool University, 111 Ren Ai Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China

,

Qun Luo

^aPrintable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China

,

Hongwei Tan

^cCollege of Chemistry, Beijing Normal University, 19 XinJieKouWai Street, HaiDian District Beijing 100875, P. R. China

,

Hai-Bo Yang

^bDepartment of Chemistry, Shanghai Key Laboratory of Green Chemistry and Chemical, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China

,

Chang-Qi Ma

^aPrintable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China

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Abstract

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Abstract

A–π–D–π–A type conjugated small molecules play an indispensable role in organic photovoltaics. Understanding the relationship between the molecular structure and performance is a fundamental question for the further rational design of high-performance organic materials. To red-shift the absorption spectrum of benzo[1,2-b:4,5-b']dithiophene (BDT) based A–π–D–π–A type compounds, an electron-donating 3,4-ethylenedioxythiophene (EDOT) moiety was introduced into the π-conjugation bridge unit. Two new compounds with EDOT next to the central BDT core (COOP-2HT-EDOT-BDT) or next to the terminal electron acceptor unit (COOP-EDOT-2HT-BDT) were synthesized and characterized. The compound COOP-2HT-EDOT-BDT showed higher molar extinction coefficient (ε_abs ^max = 1.06 × 10⁵ L mol⁻¹ cm⁻¹), lower optical band gap (E _g = 1.56 eV) and high HOMO energy level (E _HOMO = −5.08 eV) than COOP-EDOT-2HT-BDT (ε_abs ^max = 0.96 × 10⁵ L mol⁻¹ cm⁻¹, E _g = 1.71 eV, E _HOMO = −5.26 eV), which is attributed to the intensive interaction between the EDOT unit and the HOMO orbital, as confirmed by the theoretical calculation results. However, the higher power conversion efficiency of 3.58% was achieved for the COOP-EDOT-2HT-BDT:PC₆₁BM-based solar cells, demonstrating that the electron-donating EDOT unit adjacent to the electron-withdrawing end-capped group (COOP) is a better way to achieve high-performance photovoltaic materials.

Key words

organic solar cells - organic semiconductors - A–π–D–π–A small molecules - benzo[1,2-b:4,5-b′]dithiophene derivatives - 3,4-ethylenedioxythiophene

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