Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics

Joseph Cameron; Mahmoud Matar Abed; Steven J. Chapman; Neil J. Findlay; Peter J. Skabara; Peter N. Horton; Simon J. Coles

doi:10.1039/c7tc05075e

Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics

Joseph Cameron, Mahmoud Matar Abed, Steven J. Chapman, Neil J. Findlay, Peter J. Skabara, Peter N. Horton, Simon J. Coles

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Two new donor-acceptor-donor molecules, featuring either 2,1,3-benzothiadiazole (BT) or 2,1,3-benzoxadiazole (BO) and capped by benzofuranyl-thienyl groups, are presented. The structures of these novel compounds differ only in the identity of one heteroatom in the acceptor unit. Replacement of the sulfur atom in BT with oxygen results in a marked improvement in the performance of PC₆₁BM blends in bulk heterojunction organic photovoltaic (BHJ OPV) devices: a 10-fold increase in PCE is observed when switching to the BO analogue. This is partly due to a preferable morphology in the donor-fullerene blends formed upon spin-coating from chlorinated solvents.

Original language	English
Pages (from-to)	3709-3714
Number of pages	6
Journal	Journal of Materials Chemistry C
Volume	6
Issue number	14
Early online date	21 Dec 2017
DOIs	https://doi.org/10.1039/c7tc05075e
Publication status	Published - 14 Apr 2018

Funding

The authors thank the EPSRC for funding the UK National Crystallography Service (Contract Number PR150005). PJS thanks the Royal Society for a Wolfson Merit award. NJF and JC thank the EPSRC for funding (EP/N035496/1 and EP/P02744X/1). MMA and S. J. Chapman thank the American Chemical Society’s International Research Experience for Undergraduates (IREU) program which is funded by the U.S. National Science Foundation under DMR-1262908. We acknowledge the EPSRC UK National Mass Spectrometry Facility (NMSF) at Swansea University for HRMS.

Keywords

donor–acceptor−donor molecules
2,1,3-benzothiadiazole (BT)
2,1,3-benzoxadiazole (BO)
benzofuranyl-thienyl groups

Access to Document

10.1039/c7tc05075e

Cite this

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title = "Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics",

abstract = "Two new donor-acceptor-donor molecules, featuring either 2,1,3-benzothiadiazole (BT) or 2,1,3-benzoxadiazole (BO) and capped by benzofuranyl-thienyl groups, are presented. The structures of these novel compounds differ only in the identity of one heteroatom in the acceptor unit. Replacement of the sulfur atom in BT with oxygen results in a marked improvement in the performance of PC61BM blends in bulk heterojunction organic photovoltaic (BHJ OPV) devices: a 10-fold increase in PCE is observed when switching to the BO analogue. This is partly due to a preferable morphology in the donor-fullerene blends formed upon spin-coating from chlorinated solvents.",

keywords = "donor–acceptor−donor molecules, 2,1,3-benzothiadiazole (BT), 2,1,3-benzoxadiazole (BO), benzofuranyl-thienyl groups",

author = "Joseph Cameron and Abed, {Mahmoud Matar} and Chapman, {Steven J.} and Findlay, {Neil J.} and Skabara, {Peter J.} and Horton, {Peter N.} and Coles, {Simon J.}",

year = "2018",

month = apr,

day = "14",

doi = "10.1039/c7tc05075e",

language = "English",

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pages = "3709--3714",

journal = "Journal of Materials Chemistry C",

issn = "2050-7534",

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AU - Cameron, Joseph

AU - Abed, Mahmoud Matar

AU - Chapman, Steven J.

AU - Findlay, Neil J.

AU - Skabara, Peter J.

AU - Horton, Peter N.

AU - Coles, Simon J.

PY - 2018/4/14

Y1 - 2018/4/14

N2 - Two new donor-acceptor-donor molecules, featuring either 2,1,3-benzothiadiazole (BT) or 2,1,3-benzoxadiazole (BO) and capped by benzofuranyl-thienyl groups, are presented. The structures of these novel compounds differ only in the identity of one heteroatom in the acceptor unit. Replacement of the sulfur atom in BT with oxygen results in a marked improvement in the performance of PC61BM blends in bulk heterojunction organic photovoltaic (BHJ OPV) devices: a 10-fold increase in PCE is observed when switching to the BO analogue. This is partly due to a preferable morphology in the donor-fullerene blends formed upon spin-coating from chlorinated solvents.

AB - Two new donor-acceptor-donor molecules, featuring either 2,1,3-benzothiadiazole (BT) or 2,1,3-benzoxadiazole (BO) and capped by benzofuranyl-thienyl groups, are presented. The structures of these novel compounds differ only in the identity of one heteroatom in the acceptor unit. Replacement of the sulfur atom in BT with oxygen results in a marked improvement in the performance of PC61BM blends in bulk heterojunction organic photovoltaic (BHJ OPV) devices: a 10-fold increase in PCE is observed when switching to the BO analogue. This is partly due to a preferable morphology in the donor-fullerene blends formed upon spin-coating from chlorinated solvents.

KW - donor–acceptor−donor molecules

KW - 2,1,3-benzothiadiazole (BT)

KW - 2,1,3-benzoxadiazole (BO)

KW - benzofuranyl-thienyl groups

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ER -

Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics

Abstract

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Light-controlled manufacturing of semiconductor structures: a platform for next generation processing of photonic devices

Data for: "Novel Small Donor-Acceptor Molecules for OPV Devices – Investigating the Effect of Heteroatom Substitution in 2,1,3-Benzoxadiazole and 2,1,3-Benzothiadiazole "

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Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics

Abstract

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Light-controlled manufacturing of semiconductor structures: a platform for next generation processing of photonic devices

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Data for: "Novel Small Donor-Acceptor Molecules for OPV Devices – Investigating the Effect of Heteroatom Substitution in 2,1,3-Benzoxadiazole and 2,1,3-Benzothiadiazole "

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