On the Effect of Fluorination of 2,1,3-Benzothiadiazole

Handle URI:
http://hdl.handle.net/10754/550816
Title:
On the Effect of Fluorination of 2,1,3-Benzothiadiazole
Authors:
Nielsen, Christian B.; White, Andrew J. P.; McCulloch, Iain ( 0000-0002-6340-7217 )
Abstract:
The 4,7-dithieno-2,1,3-benzothiadiazole (DTBT) moiety and its fluorinated counterpart are important pi-conjugated building blocks in the field of organic electronics. Here we present a combined experimental and theoretical investigation into fundamental properties relating to these two molecular entities and discuss the potential impact on extended π-conjugated materials and their electronic properties. While the fluorinated derivative, in the solid state, packs with a smaller co-facial overlap than DTBT, we report experimental evidence for stronger optical absorption as well as stronger intra- and intermolecular contacts upon fluorination.
KAUST Department:
Physical Sciences and Engineering (PSE) Division
Citation:
On the Effect of Fluorination of 2,1,3-Benzothiadiazole 2015:150422141205007 The Journal of Organic Chemistry
Publisher:
American Chemical Society (ACS)
Journal:
The Journal of Organic Chemistry
Issue Date:
22-Apr-2015
DOI:
10.1021/acs.joc.5b00430
PubMed ID:
25901908
PubMed Central ID:
PMC4441535
Type:
Article
ISSN:
0022-3263; 1520-6904
Is Supplemented By:
Nielsen, C. B., White, A. J. P., & McCulloch, I. (2015). CCDC 1035381: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13rddn; DOI:10.5517/cc13rddn; HANDLE:http://hdl.handle.net/10754/624382; Nielsen, C. B., White, A. J. P., & McCulloch, I. (2015). CCDC 1035382: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13rdfp; DOI:10.5517/cc13rdfp; HANDLE:http://hdl.handle.net/10754/624383
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b00430
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorNielsen, Christian B.en
dc.contributor.authorWhite, Andrew J. P.en
dc.contributor.authorMcCulloch, Iainen
dc.date.accessioned2015-04-28T11:50:53Zen
dc.date.available2015-04-28T11:50:53Zen
dc.date.issued2015-04-22en
dc.identifier.citationOn the Effect of Fluorination of 2,1,3-Benzothiadiazole 2015:150422141205007 The Journal of Organic Chemistryen
dc.identifier.issn0022-3263en
dc.identifier.issn1520-6904en
dc.identifier.pmid25901908en
dc.identifier.doi10.1021/acs.joc.5b00430en
dc.identifier.urihttp://hdl.handle.net/10754/550816en
dc.description.abstractThe 4,7-dithieno-2,1,3-benzothiadiazole (DTBT) moiety and its fluorinated counterpart are important pi-conjugated building blocks in the field of organic electronics. Here we present a combined experimental and theoretical investigation into fundamental properties relating to these two molecular entities and discuss the potential impact on extended π-conjugated materials and their electronic properties. While the fluorinated derivative, in the solid state, packs with a smaller co-facial overlap than DTBT, we report experimental evidence for stronger optical absorption as well as stronger intra- and intermolecular contacts upon fluorination.en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.joc.5b00430en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b00430.en
dc.titleOn the Effect of Fluorination of 2,1,3-Benzothiadiazoleen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalThe Journal of Organic Chemistryen
dc.identifier.pmcidPMC4441535en
dc.eprint.versionPost-printen
dc.contributor.institutionDepartment of Chemistry and Centre for Plastic Elec tronics, Imperial College London, London SW7 2AZ, United Kingdom.en
kaust.authorMcCulloch, Iainen
dc.relation.isSupplementedByNielsen, C. B., White, A. J. P., & McCulloch, I. (2015). CCDC 1035381: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13rddnen
dc.relation.isSupplementedByDOI:10.5517/cc13rddnen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624382en
dc.relation.isSupplementedByNielsen, C. B., White, A. J. P., & McCulloch, I. (2015). CCDC 1035382: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13rdfpen
dc.relation.isSupplementedByDOI:10.5517/cc13rdfpen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624383en

Related articles on PubMed

All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.