Single-Acetylene Linked Porphyrin Nanorings
Author(s) -
Michel Rickhaus,
Andreas Vargas Jentzsch,
Lara Tejerina,
Isabell Grübner,
Michael Jirásek,
Timothy D. W. Claridge,
Harry L. Anderson
Publication year - 2017
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.7b10710
Subject(s) - chemistry , porphyrin , random hexamer , delocalized electron , dihedral angle , sonogashira coupling , singlet state , crystallography , acetylene , annulene , density functional theory , photochemistry , excited state , symmetry (geometry) , computational chemistry , molecule , atomic physics , organic chemistry , palladium , hydrogen bond , physics , catalysis , geometry , mathematics
The synthesis of ethyne-linked porphyrin nanorings has been achieved by template-directed Sonogashira coupling. The cyclic hexamer and octamer are predicted by density functional theory to adopt low symmetry conformations, due to dihedral twists between neighboring porphyrin units, but their symmetries are effectively D 6h and D 8h , respectively, in solution by 1 H NMR. The fluorescence spectra indicate that the singlet excited states of these nanorings are highly delocalized.
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