Ambidextrous Catalytic Access to Dithieno[3,2-b:2 ',3 '-d]thiophene (DTT) Derivatives by Both Palladium-Catalyzed C-S and Oxidative Dehydro C-H Coupling

A modular two-step synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) derivatives by C-S cross-coupling and oxidative dehydro C-H coupling is herein described. Dibenzo[d,d']thieno[3,2-b;4,5-b']dithiophene (DBTDT) and associated two donor (anisyl) and acceptor (acetyl) substitute...

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Published inOrganic letters Vol. 16; no. 16; pp. 4086 - 4089
Main Authors Oechsle, Peter, Paradies, Jan
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.08.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HIGH-PERFORMANCE
ORGANIC TRANSISTORS
SELENOPHENE-BASED HETEROACENES
SENSITIZED SOLAR-CELLS
RING OSCILLATORS
ONE-POT SYNTHESIS
FUSED THIOPHENES
THIN-FILM TRANSISTORS
OLIGOTHIOPHENES
FIELD-EFFECT TRANSISTORS
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Summary:A modular two-step synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) derivatives by C-S cross-coupling and oxidative dehydro C-H coupling is herein described. Dibenzo[d,d']thieno[3,2-b;4,5-b']dithiophene (DBTDT) and associated two donor (anisyl) and acceptor (acetyl) substituted DTT derivatives were synthesized by palladium-catalyzed cross-coupling sequences in 17% to 71% yield over two steps. The 5,5'-disubstituted DTT derivatives were characterized in terms of their photophysical (UV and fluorescence spectroscopy) and electrophysical (cyclovoltammography) properties.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol501752f