Heteroannulated acceptors based on benzothiadiazole

Timothy C. Parker, Dinesh G. Patel, Karttikay Moudgil, Stephen Barlow, Chad Risko, Jean Luc Brédas, John R. Reynolds, Seth R. Marder

Research output: Contribution to journalReview articlepeer-review

130 Scopus citations


Increasing the acceptor strength of the widely used acceptor benzothiadiazole (BT) by extending the heterocyclic core is a promising strategy for developing new and stronger acceptors for materials in organic electronics and photonics. In recent years, such heteroannulated BT acceptors have been incorporated into a wide variety of materials that have been used in organic electronic and photonic devices. This review critically assesses the properties of these materials. Although heteroannulation to form acceptors, such as benzo[1,2-c:4,5-c′]bis[1,2,5]thiadiazole (BBT), does result in materials with significantly higher electron affinity (EA) relative to BT, in many cases the extended BT systems also exhibit lower ionization energy (IE) than BT. Both the significantly higher EA and lower IE limit the efficacy of these materials in applications such as bulk heterojunction organic photovoltaics (BHJ-OPV) based on C60. Although the relatively high EA may enable some applications such as air stable organic field effect transistors (OFET), more widespread use of heteroannulated BT acceptors will likely require the ability to moderate or retain the high EA while increasing IE.

Original languageEnglish
Pages (from-to)22-36
Number of pages15
JournalMaterials Horizons
Issue number1
StatePublished - Jan 2015

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2015.

ASJC Scopus subject areas

  • General Materials Science
  • Mechanics of Materials
  • Process Chemistry and Technology
  • Electrical and Electronic Engineering


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