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Hydrindacene‐Based Acetylenic Macrocycles with Horizontally and Vertically Ordered Functionality Arrays
Author(s) -
Kawai Hidetoshi,
Utamura Tatsuya,
Motoi Erina,
Takahashi Tomoko,
Sugino Hiroyoshi,
Tamura Manabu,
Ohkita Masakazu,
Fujiwara Kenshu,
Saito Takao,
Tsuji Takashi,
Suzuki Takanori
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200716
Subject(s) - trimer , dimer , conjugated system , molecule , chemistry , flexibility (engineering) , crystallography , perpendicular , stereochemistry , polymer , organic chemistry , mathematics , geometry , statistics
The macrocyclization of 2,6‐diethynyl hydrindacenes ( 1 ) with functional groups at mutually perpendicular positions results in the formation of novel macrocycles which, as a result of the hindered rotation of the hydrindacene units, possess directionally persistent peripheral functionalities. The two hydrindacene units in the dimer macrocycle ( 2 ) have been shown to interact electronically through their respective butadiyne moieties, whereas the trimer macrocycle ( 3 ) demonstrates a moderate degree of geometrical flexibility as a result of the five‐membered hydrindacene rings. In addition, these trimer macrocycles contain a central cavity suitably sized for the inclusion of various solvent molecules. These new macrocycles can be further modified by introducing π‐conjugated side groups, such as styryl and thienyl groups, as well as by attaching a variety of peripheral ester groups.