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 article

66 Citations (Scopus)

Abstract

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 (US)
Pages (from-to)22-36
Number of pages15
JournalMaterials Horizons
Volume2
Issue number1
DOIs
StatePublished - Jan 1 2015

Fingerprint

Electron affinity
Ionization potential
Organic field effect transistors
Photonic devices
Thiadiazoles
Photonics
Heterojunctions
Electronic equipment
benzo-1,2,3-thiadiazole
Air

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Mechanics of Materials
  • Process Chemistry and Technology
  • Electrical and Electronic Engineering

Cite this

Parker, T. C., Patel, D. G., Moudgil, K., Barlow, S., Risko, C., Brédas, J. L., ... Marder, S. R. (2015). Heteroannulated acceptors based on benzothiadiazole. Materials Horizons, 2(1), 22-36. https://doi.org/10.1039/c4mh00102h
Parker, Timothy C. ; Patel, Dinesh G. ; Moudgil, Karttikay ; Barlow, Stephen ; Risko, Chad ; Brédas, Jean Luc ; Reynolds, John R. ; Marder, Seth R. / Heteroannulated acceptors based on benzothiadiazole. In: Materials Horizons. 2015 ; Vol. 2, No. 1. pp. 22-36.
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Parker, TC, Patel, DG, Moudgil, K, Barlow, S, Risko, C, Brédas, JL, Reynolds, JR & Marder, SR 2015, 'Heteroannulated acceptors based on benzothiadiazole', Materials Horizons, vol. 2, no. 1, pp. 22-36. https://doi.org/10.1039/c4mh00102h

Heteroannulated acceptors based on benzothiadiazole. / Parker, Timothy C.; Patel, Dinesh G.; Moudgil, Karttikay; Barlow, Stephen; Risko, Chad; Brédas, Jean Luc; Reynolds, John R.; Marder, Seth R.

In: Materials Horizons, Vol. 2, No. 1, 01.01.2015, p. 22-36.

Research output: Contribution to journalReview article

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AU - Parker, Timothy C.

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AU - Moudgil, Karttikay

AU - Barlow, Stephen

AU - Risko, Chad

AU - Brédas, Jean Luc

AU - Reynolds, John R.

AU - Marder, Seth R.

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Parker TC, Patel DG, Moudgil K, Barlow S, Risko C, Brédas JL et al. Heteroannulated acceptors based on benzothiadiazole. Materials Horizons. 2015 Jan 1;2(1):22-36. https://doi.org/10.1039/c4mh00102h