Synthesis and Isomeric Effects of Ladder-Type Alkylated Terbenzodithiophene Derivatives

Yung Lung Chen, Jhih Yang Hsu, Fang Yu Lin, Yu Ying Lai, Hsiao Chieh Chou, Yen-Ju Cheng*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A new class of heptacyclic ladder-type terbenzodithiophene (TBDT) structures merging three fused benzodithophenes was developed. Two TBDT conjugated isomers, named as syn-TBDT and anti-TBDT, where the two thienyl rings in the outmost BDT units are in the syn- and anti-fashion, are designed. Two decyl groups are introduced to their 6,13 and 7,14-positions to form four isomeric 6,13-syn-TBDT, 7,14-syn-TBDT, 6,13-anti-TBDT, and 7,14-anti-TBDT structures which are constructed by the DBU-induced 6-benzannulation involving propargyl-allenyl isomerization of the dieneyne moieties in the corresponding precursors followed by 6π-electrocyclization/aromatization, while isomeric TD-syn-TBDT and TD-anti-TBDT with four decyl groups substituted at 6,7,13,14-positions are synthesized via palladium-catalyzed dialkylacetylene insertion/C-H arylation of the corresponding iodobiaryl precursors. The intrinsic properties can be modulated by molecular manipulation of the main-chain and side-chain isomeric structures. anti-TBDT derivatives exhibit higher melting points, larger bandgaps, stronger intermolecular interactions, and higher mobility than the corresponding syn-TBDT analogues. These molecules can be further utilized as building blocks to make various TBDT-based materials for optoelectronic applications.

Original languageEnglish
Pages (from-to)2534-2542
Number of pages9
JournalJournal of Organic Chemistry
Volume81
Issue number6
DOIs
StatePublished - 18 Mar 2016

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