Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization

The synthesis of C 4- and C 2-symmetrical [8]­cycloparaphenylene (CPP)-octacarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-cyclotrimerization and subsequent reductive aromatization. The C 4-symmetrical octa-tert-butyl [8]­CPP-octacarboxylate...

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Bibliographic Details
Published in:Organic letters 2017-06, Vol.19 (11), p.2993-2996
Main Authors: Hayase, Norihiko, Miyauchi, Yuta, Aida, Yukimasa, Sugiyama, Haruki, Uekusa, Hidehiro, Shibata, Yu, Tanaka, Ken
Format: Article
Language:English
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Summary:The synthesis of C 4- and C 2-symmetrical [8]­cycloparaphenylene (CPP)-octacarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-cyclotrimerization and subsequent reductive aromatization. The C 4-symmetrical octa-tert-butyl [8]­CPP-octacarboxylate forms a dimer in which eight ester moieties face each other. The dimers are aligned so as to make a one-dimensional column with a channel structure inside. Both absorption and fluorescence maxima of [8]­CPP-octacarboxylates in CHCl3 were significantly blue-shifted compared to those of [8]­CPP due to the presence of eight electron-withdrawing ester moieties.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01231