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meso ‐3,5‐Bis(trifluoromethyl)phenyl‐Substituted Expanded Porphyrins: Synthesis, Characterization, and Optical, Electrochemical, and Photophysical Properties
Author(s) -
Kang Soonchul,
Hayashi Hironobu,
Umeyama Tomokazu,
Matano Yoshihiro,
Tkachenko Nikolai V.,
Lemmetyinen Helge,
Imahori Hiroshi
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800229
Subject(s) - trifluoromethyl , electrochemistry , characterization (materials science) , chemistry , combinatorial chemistry , materials science , nanotechnology , organic chemistry , electrode , alkyl
Trifluoroacetic acid‐catalyzed condensation of pyrrole with electron‐deficient and sterically hindered 3,5‐bis(trifluoromethyl)benzaldehyde results in the unexpected production of a series of meso ‐3,5‐bis(trifluoromethyl)phenyl‐substituted expanded porphyrins including [22]sapphyrin 2 , N ‐fused [22]pentaphyrin 3 , [26]hexaphyrin 4 , and intact [32]heptaphyrin 5 together with the conventional 5,10,15,20‐tetrakis(3,5‐bis(trifluoromethyl)phenyl)porphyrin 1 . These expanded porphyrins are characterized by mass spectrometry, 1 H NMR spectroscopy, UV/Vis/NIR absorption spectroscopy, and fluorescence spectroscopy. The optical and electrochemical measurements reveal a decrease in the HOMO–LUMO gap with increasing size of the conjugated macrocycles, and in accordance with the trend, the deactivation of the excited singlet state to the ground state is enhanced.