Synthesis and properties of pteridine-2,4-dione-functionalised oligothiophenes

Alan A. Wiles; Brian Fitzpatrick; Niall A. McDonald; Mary Margaret Westwater; De-Liang Long; Bernd Ebenhoch; Vincent M. Rotello; Ifor D. W. Samuel; Graeme Cooke

doi:10.1039/C5RA22402K

Synthesis and properties of pteridine-2,4-dione-functionalised oligothiophenes

Alan A. Wiles, Brian Fitzpatrick, Niall A. McDonald, Mary Margaret Westwater, De-Liang Long, Bernd Ebenhoch, Vincent M. Rotello, Ifor D. W. Samuel, Graeme Cooke

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Abstract

The synthesis of acceptor-functionalised oligothiophene derivatives (t3, t6, t7, t8) is described, where the pteridine-2,4-dione acceptor units are arranged symmetrically in derivatives t6-t8. The symmetrical arrangement of acceptor units stems from the ability to selectively brominate the conjugated thiophene moiety of building block t3. Upon increasing the conjugation by going from t3 to t8, a significant increase in absorption toward the near-infrared region and a simultaneous narrowing of the HOMO/LUMO gap occurs, which may promote their future application as optoelectronic materials.

Original language	English
Pages (from-to)	7999-8005
Number of pages	7
Journal	RSC Advances
Volume	6
Issue number	10
Early online date	19 Jan 2016
DOIs	https://doi.org/10.1039/C5RA22402K
Publication status	Published - 2016

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10.1039/C5RA22402KLicence: CC BY

Samuel_2016_RSCA_Synthesis_CCBY
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
Final published version, 1.01 MBLicence: CC BY

Cite this

@article{ecc97bb1858e4d0c91e8ed3f6d185196,

title = "Synthesis and properties of pteridine-2,4-dione-functionalised oligothiophenes",

abstract = "The synthesis of acceptor-functionalised oligothiophene derivatives (t3, t6, t7, t8) is described, where the pteridine-2,4-dione acceptor units are arranged symmetrically in derivatives t6-t8. The symmetrical arrangement of acceptor units stems from the ability to selectively brominate the conjugated thiophene moiety of building block t3. Upon increasing the conjugation by going from t3 to t8, a significant increase in absorption toward the near-infrared region and a simultaneous narrowing of the HOMO/LUMO gap occurs, which may promote their future application as optoelectronic materials.",

author = "Wiles, {Alan A.} and Brian Fitzpatrick and McDonald, {Niall A.} and Westwater, {Mary Margaret} and De-Liang Long and Bernd Ebenhoch and Rotello, {Vincent M.} and Samuel, {Ifor D. W.} and Graeme Cooke",

note = "GC and IDWS thank the EPSRC for funding (EP/I00243X/1). VR thanks the NSF (CHE-1307021). IDWS also acknowledges support from a Royal Society Wolfson Research Merit Award.",

year = "2016",

doi = "10.1039/C5RA22402K",

language = "English",

volume = "6",

pages = "7999--8005",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "10",

}

TY - JOUR

T1 - Synthesis and properties of pteridine-2,4-dione-functionalised oligothiophenes

AU - Wiles, Alan A.

AU - Fitzpatrick, Brian

AU - McDonald, Niall A.

AU - Westwater, Mary Margaret

AU - Long, De-Liang

AU - Ebenhoch, Bernd

AU - Rotello, Vincent M.

AU - Samuel, Ifor D. W.

AU - Cooke, Graeme

N1 - GC and IDWS thank the EPSRC for funding (EP/I00243X/1). VR thanks the NSF (CHE-1307021). IDWS also acknowledges support from a Royal Society Wolfson Research Merit Award.

PY - 2016

Y1 - 2016

N2 - The synthesis of acceptor-functionalised oligothiophene derivatives (t3, t6, t7, t8) is described, where the pteridine-2,4-dione acceptor units are arranged symmetrically in derivatives t6-t8. The symmetrical arrangement of acceptor units stems from the ability to selectively brominate the conjugated thiophene moiety of building block t3. Upon increasing the conjugation by going from t3 to t8, a significant increase in absorption toward the near-infrared region and a simultaneous narrowing of the HOMO/LUMO gap occurs, which may promote their future application as optoelectronic materials.

AB - The synthesis of acceptor-functionalised oligothiophene derivatives (t3, t6, t7, t8) is described, where the pteridine-2,4-dione acceptor units are arranged symmetrically in derivatives t6-t8. The symmetrical arrangement of acceptor units stems from the ability to selectively brominate the conjugated thiophene moiety of building block t3. Upon increasing the conjugation by going from t3 to t8, a significant increase in absorption toward the near-infrared region and a simultaneous narrowing of the HOMO/LUMO gap occurs, which may promote their future application as optoelectronic materials.

UR - http://www.rsc.org/suppdata/c5/ra/c5ra22402k/c5ra22402k1.pdf

U2 - 10.1039/C5RA22402K

DO - 10.1039/C5RA22402K

M3 - Article

SN - 2046-2069

VL - 6

SP - 7999

EP - 8005

JO - RSC Advances

JF - RSC Advances

IS - 10

ER -

Synthesis and properties of pteridine-2,4-dione-functionalised oligothiophenes

Abstract

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