Open AccessSynthesis, properties and reactivity of an ortho-phenylene-cyclopentene-bridged tetrapyrrole
Author(s) -
Yuki Morimoto,
Atsuhiro Osuka,
Takayuki Tanaka
Publication year - 2021
Publication title -
journal of porphyrins and phthalocyanines
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.322
H-Index - 64
eISSN - 1099-1409
pISSN - 1088-4246
DOI - 10.1142/s1088424621500553
Subject(s) - tetrapyrrole , chemistry , cyclopentene , moiety , porphyrin , phenylene , pyrrole , fulvene , photochemistry , isoindole , photochromism , stereochemistry , polymer chemistry , organic chemistry , polymer , enzyme , catalysis
Increasing the number of meso-methine carbons of porphyrin has led to a creation of a series of vinylogous expanded porphyrins, while the introduction of an ortho-phenylene-unit as a pyrrole-connecting two-carbon bridge usually leads to prevention of effective macrocyclic conjugation. Cyclopentene can serve as a conjugative bridge to increase the macrocyclic conjugation owing to its cis-geometry. In this work, ortho-phenylene-cyclopentene-bridged tetrapyrrole 5 was prepared on the basis of a coupling strategy. The tetrapyrrole 5 exhibited slightly more conjugative features as compared to ortho-phenylene-bridged tetrapyrrole 4. Oxidation of 5 with [bis(trifluoroacetoxy)iodo]benzene (PIFA) at low temperature afforded a partly fused tetrapyrrolic compound 9 having a spiro-connected pyrrolo[2,1-[Formula: see text]]isoindole moiety.