Direct heteroarylation of β-protected dithienosilole and dithienogermole monomers with thieno[3,4-c]pyrrole-4,6-dione and furo[3,4-c]pyrrole-4,6-dione

Download
  1. Get@NRC: Direct heteroarylation of β-protected dithienosilole and dithienogermole monomers with thieno[3,4-c]pyrrole-4,6-dione and furo[3,4-c]pyrrole-4,6-dione (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1039/c3py21138j
AuthorSearch for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titlePolymer Chemistry
ISSN1759-9954
Volume4
Issue20
Pages52525260; # of pages: 9
SubjectArylation reactions; Bulk heterojunction solar cells; Cross coupling reactions; Cross-linked materials; Cross-linked polymers; Heteroarylation; Organic solar cell; Polymerization reaction; Crosslinking; Heterojunctions; Monomers; Polymerization; Polymers; Solar cells; Aromatic compounds
AbstractDirect C-H bond arylation reactions between heteroarenes and aryl halides provide an atom-economical and "green" alternative to standard cross-coupling reactions (Stille, Suzuki, etc.). Unfortunately, this reaction is not selective and more than one type of C-H bond may react, which, during polymerization reactions, can lead to cross-linked materials. This paper reports the preparation of PDTSiTPD and PDTGeTPD, which have exhibited high efficiencies in organic solar cells, using direct (hetero)arylation polymerization methodologies. In order to circumvent side reactions leading to cross-linked polymers, a number of new dithieno[3,2-b:2′,3′-d]silole (DTSi) monomers were prepared where the β-positions were blocked with alkyl chains and the alkyl groups on the heteroatom were modified. Co-polymers were synthesized with N-alkylthieno[3,4-c]pyrrole-4,6-dione (TPD) and the oxygen congener, N-alkylfuro[3,4-c]pyrrole-4,6-dione (FPD). However, the resulting polymers were not planar, and conjugation of the backbone was disrupted. An efficiency of 1.7% was achieved in bulk heterojunction solar cells (BHJ-SCs). © 2013 The Royal Society of Chemistry.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21270608
Export citationExport as RIS
Report a correctionReport a correction
Record identifier839f7551-819c-4ce2-a95e-e15908d3e107
Record created2014-02-17
Record modified2016-05-09
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)