標題: Synthesis and Isomeric Effects of Ladder-Type Alkylated Terbenzodithiophene Derivatives
作者: Chen, Yung-Lung
Hsu, Jhih-Yang
Lin, Fang-Yu
Lai, Yu-Ying
Chou, Hsiao-Chieh
Cheng, Yen-Ju
應用化學系
Department of Applied Chemistry
公開日期: 18-Mar-2016
摘要: 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 6 pi-electro-cyclization/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.
URI: http://dx.doi.org/10.1021/acs.joc.6b00101
http://hdl.handle.net/11536/133466
ISSN: 0022-3263
DOI: 10.1021/acs.joc.6b00101
期刊: JOURNAL OF ORGANIC CHEMISTRY
Volume: 81
Issue: 6
起始頁: 2534
結束頁: 2542
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