4.7 Article

Donor acceptor acceptor-based non-fullerene acceptors comprising terminal chromen-2-one functionality for efficient bulk-heterojunction devices

Journal

DYES AND PIGMENTS
Volume 146, Issue -, Pages 502-511

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2017.07.047

Keywords

Solution-processable; Triphenylamine; Chromen-2-one; Bulk-heterojunction; Donor-acceptor-acceptor; Solar cells

Funding

  1. Australian Research Council (ARC), Australia, under a Future Fellowship Scheme [FT110100152]
  2. Alfred Deakin Fellowship Scheme at the IFM, Deakin University, Waurn Ponds Victoria Australia
  3. TAPSUN programme [NWP0054]
  4. CSIR, New Delhi

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Two simple semiconducting donor atceptor acceptor (D-A(1)-A) modulat small molecule, nonfullerene electron acceptors, 2-(4-(diphenylarnino)pheny1)-3-(4-((2-oxo-2H-chromen-3-yl)ethynyl) phenyl)buta-1,3-diene-1,1,4,4-tetracarbonitrile (P2) and 2-(4-(3,3-dicyano-1-(4-(diphenylamino) pheny1)-2-(44(2-oxo-2H-chromen-3-yl)ethynyl)phenyl)allylidene)cyclohexa-2,5-dien-1-ylidene)malononitrile (P3), were designed, synthesized and characterized for application in solution-processable bulk-beterojunction solar cells. The optoelectronic and photovoltaic properties of P2 and P3 were directly compared with those of a structural analogue, 3-((4-((4-(diphenylamino)phenyl)ethynyl)phenyl) ethynyl)-2H-chromen-2-one (P1), which was designed based on a D A format. All of these new materials comprised an electron rich triphenylamine (TPA) donor core (D) and electron deficient chromen-2one terminal core (A). In the simple D A system, IPA and chromenone were the terminal functionalities, whereas in the D A1 A system, tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ) derived functionalities were incorporated as Al units by keeping the D/A units constant. The inclusion of Al was primarily done to indute.cross-conjugation within the molecular backbone and hence.to generate low band gap targets. The physical and optoelectronic properties were characterized by ultraviolet visible (UV Vis), thermograviMetric analysis, photo -electron spectroscopy in air and cyclic voltammetry. These new materials exhibited broadened absorption spectra, for instance panchromatic absorbance in case of P3, excellent solubility and thermal stability, and energy levels matching those of the conventional and routinely used donor polymer poly(3-hexyl thiophene) (P3HT). Solution-processable bulk-heterojunction devices were fabricated with P1, P2 and P3 as non-fullerene electron acceptors. Studies on the photovoltaic properties revealed that the best P3HT: P3 -based device showed an impressive enhanced power conversion efficiency of 4.21%, an increase of around two -fold with respect to the efficiency of the best P3HT: P1 -based device (2.28%). Our results clearly demOnstrate that the D A1 A type small molecules are promising non-fullerene electron acceptors in the research field of organic solar cells. (C) 2017 Elsevier Ltd. All rights reserved.

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