Oxacycle fused [1]benzothieno[3,2‐b][1]benzothiophene derivatives : synthesis, electronic structure, electrochemical properties, ionisation potential, and crystal structure

Mohankumar, Meera and Chattopadhyay, Basab and Sanguinet, Lionel and Kennedy, Alan R. and Lemaur, Vincent and Cornil, Jérôme and Fenwick, Oliver and Samori, Paolo and Geerts, Yves and Hadji, Rachid (2018) Oxacycle fused [1]benzothieno[3,2‐b][1]benzothiophene derivatives : synthesis, electronic structure, electrochemical properties, ionisation potential, and crystal structure. ChemPlusChem. ISSN 2192-6506 (https://doi.org/10.1002/cplu.201800346)

Preview

Text. Filename: Mohankumar_etal_CEC_2018_electrochemical_properties_ionisation_potential_and_crystal_structure.pdf Accepted Author Manuscript Download (2MB)| Preview

Abstract

he molecular properties of [1]benzothieno[3,2‐b][1]benzothiophene (BTBT) are vulnerable to the structural modifications which in turn are decided by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover the properties of this molecule. To address this, we have attempted heteroatom (oxygen) functionalization of BTBT by a concise and easily scalable synthesis. Four‐fold hydroxy substituted BTBT is the key intermediate, from which the compounds 2,3,7,8‐ bis(ethylenedioxy)‐[1]benzothieno[3,2‐b][1]benzothiophene and 2,3,7,8‐ bis(methylenedioxy)‐[1]benzothieno[3,2‐b][1]benzothiophene are synthesized. The difference in ether functionalities on the BTBT scaffold influences the ionisation potential values substantially. The crystal structure reveals the transformation of the herringbone motif in bare BTBT towards π stacked columns in the newly synthesized derivatives. The results are further elaborated with the aid of quantum chemical calculations.

• Share and Export
  

  RDF+XMLBibTeXRIOXX2 XMLRDF+N-TriplesJSONDublin CoreAtomSimple MetadataReferMETSHTML CitationASCII CitationOpenURL ContextObjectEndNoteOpenURL ContextObject in SpanMODSMPEG-21 DIDLEP3 XMLData Cite XMLRIS (EndNote Online, Zotero, Ref manager, etc)RDF+N3Multiline CSV
• Item metadata

  Item type:	Article
  ID code:	65649
  Dates:	Date Event 2 October 2018 Published 2 October 2018 Published Online 28 September 2018 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	03 Oct 2018 13:17
  Last modified:	18 Apr 2024 00:23
  URI:	https://strathprints.strath.ac.uk/id/eprint/65649