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Interaction Between Terminal Zinc–Porphyrins in a U‐Shaped Trimeric Porphyrin Array Bearing Chiral Amino Acid Tails
Author(s) -
Arai Toru,
Takei Kiyoshi,
Ogawa Yoshifumi,
Nishino Norikazu
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500183
Subject(s) - porphyrin , free base , chemistry , zinc , atropisomer , pyrrole , stereochemistry , crystallography , polymer chemistry , photochemistry , organic chemistry , salt (chemistry)
A U‐shaped trimeric porphyrin array with a zinc/free‐base/zinc arrangement ( 5ZFZ ) and its derivatives were synthesized in order to investigate the interacting porphyrins in organic solvents. The porphyrin array is comprised of an αα‐atropisomeric bis( ortho ‐aminophenyl)porphyrin free‐base as the template, a pair of zinc–porphyrins at the termini, achiral glycine spacers linking the porphyrins, and chiral L ‐leucine derivatives attached to the template in the opposite direction of the zinc–porphyrins. 1 H NMR (high‐field shifts of some pyrrole signals), UV/Vis (split Soret band), and CD spectra (exciton‐coupled Cotton effect) show the close assembly of the terminal zinc–porphyrins of 5ZFZ in CDCl 3 and CH 2 Cl 2 . In contrast, the characteristic spectra for the interacting porphyrins do not appear for the trimeric array with three free‐base porphyrins ( 5F 3 ) and the dimeric array with a zinc/free‐base arrangement ( 9ZF ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)