The Preparation of a Sterically Hindered s-Tetrazine and Its Conjugated Polymers

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DOIResolve DOI: http://doi.org/10.1002/pola.24774
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TypeArticle
Journal titleJournal of Polymer Science Part A : Polymer Chemistry
Subjects-tetrazine; steric hindrance; conjugated polymer; narrow band gap; bulk heterojunction; solar cell
AbstractWe demonstrated, for the first time, that dithienyl-s-tetrazine (TTz) with hexyl group at the 3-position of thiophene rings can be prepared using a modified sulfur-assisted Pinner synthesis. Although the hexyl group creates large steric hindrance to this ring formation reaction, and the reaction under a traditional reaction condition only produces trace amount of the target product, the yield of this reaction under a modified reaction condition using anhydrous hydrazine at 68 ˚C can reach 65%. Two new copolymers of TTz and cyclepentaditiophene (CPDT) with hexyl or 2-ethylhexyl groups attached to its 4-position have been prepared. The polymer films show a broad light absorption attributing to the large distribution of effective conjugating length of polymer chain in the film due to the low steric hindrance for the rotation of the monomer units. The polymers also show a narrow band gap and a deep HOMO level, which are desirable for generating an efficient light absorption and a larger open circuit voltage (Voc) of the resulting solar cell devices.
Publication date
LanguageEnglish
AffiliationNRC Institute for Chemical Process and Environmental Technology; National Research Council Canada
Peer reviewedYes
NRC number52824
NPARC number18215932
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Record identifier41b1bdf5-258b-421f-b136-ae6b1f097b1d
Record created2011-07-06
Record modified2017-03-23
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