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Trimeric and Tetrameric Electron‐Deficient Porphyrin Tapes
Author(s) -
Mori Hirotaka,
Kim Taeyeon,
Kim Dongho,
Osuka Atsuhiro
Publication year - 2016
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.201600241
Subject(s) - porphyrin , polarizability , absorption (acoustics) , photochemistry , absorption spectroscopy , crystallography , chemistry , materials science , molecule , organic chemistry , optics , physics , composite material
New hybrid porphyrin tapes comprising meso ‐3,5‐di‐ tert‐ butylphenyl‐substituted Zn II ‐porphyrins ( D ) and meso ‐pentafluorophenyl‐substituted Zn II ‐porphyrins ( A ) were synthesized via cross‐condensation of meso ‐formyl porphyrins 1 , 5 , and 9 with oligopyrromethanes 2 and 6 as key steps. These hybrid tapes exhibit improved solubilities and enhanced chemical stability as compared with original D n porphyrin tapes, and all display remarkably coplanar structures favorable for π‐conjugation. The absorption spectrum of ADDA displays Q‐like bands at 1400 and 1657 nm with a vibronic structure characteristic of porphyrinoids. The cyclic voltammograms exhibited positively shifted oxidation and reduction waves in the order of DDD < DAD < ADA < AAA . Tetrameric tape ADDA displays five reversible waves in a narrow range of 1.13 V. Two‐photon absorption (TPA) measurement confirmed that the π‐conjugation path is extended from 12 to ADDA and the molecular polarizability of ADA is larger than that of AAA .