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Thiophene‐Fused Dinaphthopentaphenes: Versatile Applications of 1,2‐Bis(pyren‐2‐yl)aromatics in the Synthesis of π‐Expanded Molecules
Author(s) -
Hossain Md. Awlad,
Yamashita Kenichi,
Hirabayashi Kazunori,
Shimizu Toshio,
Goto Kenta,
Sugiura Kenichi
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700152
Subject(s) - helicene , thiophene , enantiomer , molecule , suzuki reaction , chemistry , pyrene , boronic acid , absorption (acoustics) , combinatorial chemistry , photochemistry , organic chemistry , stereochemistry , materials science , aryl , alkyl , composite material
Thiophene‐fused dinaphtho[8,1,2‐opq:2′,1′,8′‐uva]pentaphenes (DNPPs) were synthesized and characterized by using our previously reported strategy. The Suzuki‐Miyaura coupling of the boronic acid ester of pyrene with dibromothiophenes, 2,3‐dibromo‐ and 3,4‐dibromothiophenes, afforded the corresponding bis(pyren‐2‐yl)thiophenes. The subsequent oxidation reaction afforded the desired π‐expanded molecules. Reflecting the DNPP moieties, the obtained molecules show properties characteristic of π‐expanded molecules, such as amphoteric multiredox behaviors and light absorption in the visible region. The oxidized product of 3,4‐bis(pyren‐2‐yl)thiophene, which contains an ortho ‐quinoidal structure, i. e., benzo[ c ]thiophene, was isolated and spectroscopically characterized. Because these molecules possess the [5]helicene structure, optical resolution of enantiomers has been carried out using high‐performance liquid chromatography.