Premium
Triaminotriazines—photophysical investigations of a porphyrin‐appended triazine receptor with a naphthalene diimide guest
Author(s) -
Ghiggino Kenneth P.,
Hutchison James A.,
Langford Steven J.,
Latter Melissa J.,
Takezaki Makoto
Publication year - 2006
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1026
Subject(s) - chemistry , porphyrin , cyanuric chloride , chromophore , supramolecular chemistry , photochemistry , photoinduced electron transfer , quenching (fluorescence) , hydrogen bond , naphthalene , pyrrole , combinatorial chemistry , electron transfer , fluorescence , polymer chemistry , molecule , organic chemistry , physics , quantum mechanics
A modular synthetic approach to preparing a family of triaminotriazine receptors bearing porphyrin chromophores is described. The porphyrin‐appended triaminotriazines are prepared in a stepwise manner employing either cyanuric chloride or fluoride and 5‐(4′‐aminophenyl)‐10,15,20‐triphenylporphyrin in the first step. Reaction of the porphyrintriazine with excess 1‐pentylamine leads to a triazine core programmed for three‐point hydrogen bonding. Addition of a complementary naphthalene diimide yields a supramolecular donor–acceptor dyad. Photophysical studies in CH 2 Cl 2 solvent show efficient quenching of porphyrin fluorescence within the dyad, consistent with an electron transfer process. Copyright © 2006 John Wiley & Sons, Ltd.