Ring-fusion As a Perylenediimide Dimer Design Concept for High-performance Non-fullerene Organic Photovoltaic Acceptors

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Jul 13

PMID 29997846

Citations 14

Authors

Patrick E Hartnett

H S S Ramakrishna Matte

Nicholas D Eastham

Nicholas E Jackson

Yilei Wu

Lin X Chen

Mark A Ratner

Robert P H Chang

Mark C Hersam

Michael R Wasielewski

Tobin J Marks

Affiliations

Soon will be listed here.

Abstract

A series of perylenediimide (PDI) dimers are evaluated as acceptors for organic photovoltaic (OPV) cells. The materials are characterized using a wide variety of physical and computational techniques. These dimers are first linked at the bay position of each PDI molecule an aromatic spacer; subsequent photocyclization affords ring-fused dimers. Thus, photocyclization of the thiophene-linked dimer 2,5-bis-[,'-bis-perylenediimide-1-yl]-thiophene () affords the twisted acceptor [2,3-:2',3'-]-bis-[,'-bis-perylenediimide-1,12-yl]-thiophene (), while photocyclization of the thienothiophene-linked dimer, 2,5-bis-[,'-bis-perylenediimide-1-yl]-thienothiophene () affords the planar acceptor [2,3-:2',3'-]-bis-[,'-bis-perylenediimide-1,12-yl]-thienothiophene (). Furthermore, a dimer linked by a phenylene group, 1,4-bis-[,'-bis-perylenediimide-1-yl]-benzene (), can be selectively photocyclized to form either the twisted dimer, [1,2:3,4]-bis-[,'-bis-perylenediimide-1,12-yl]-benzene () or the planar dimer [1,2:4,5]-bis-[,'-bis-perylenediimide-1,12-yl]-benzene (). Ring-fusion results in increased electronic coupling between the PDI units, and increased space-charge limited thin film electron mobility. While charge transport is efficient in bulk-heterojunction blends of each dimer with the polymeric donor , in the case of the twisted dimers ring fusion leads to a significant decrease in geminate recombination, hence increased OPV photocurrent density and power conversion efficiency. This effect is not observed in planar dimers where ring fusion leads to increased crystallinity and excimer formation, decreased photocurrent density, and decreased power conversion efficiency. These results argue that ring fusion is an effective approach to increasing OPV bulk-heterojunction charge carrier generation efficiency in PDI dimers as long as they remain relatively amorphous, thereby suppressing excimer formation and coulombically trapped charge transfer states.

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