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Synthesis of Five‐Porphyrin Nanorings by Using Ferrocene and Corannulene Templates
Author(s) -
Liu Pengpeng,
Hisamune Yutaka,
Peeks Martin D.,
Odell Barbara,
Gong Juliane Q.,
Herz Laura M.,
Anderson Harry L.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602909
Subject(s) - corannulene , porphyrin , nanoring , pentamer , template , ferrocene , chemistry , conjugated system , fullerene , photochemistry , crystallography , materials science , nanotechnology , organic chemistry , electrochemistry , polymer , biochemistry , electrode
The smallest and most strained member of a family of π‐conjugated cyclic porphyrin oligomers was synthesized by using pentapyridyl templates based on ferrocene and corannulene. Both templates are effective for directing the synthesis of the butadiyne‐linked cyclic pentamer, despite the fact that the radii of their N5 donor sets are too small by 0.5 Å and 0.9 Å, respectively (from DFT calculations). The five‐porphyrin nanoring exhibits a structured absorption spectrum and its fluorescence extends to 1200 nm, reflecting strong π conjugation and Herzberg–Teller vibronic coupling.