Triaminotriazines—photophysical investigations of a porphyrin‐appended triazine receptor with a naphthalene diimide guest | Zendy

Ghiggino Kenneth P. | Zendy; Hutchison James A. | Zendy; Langford Steven J. | Zendy; Latter Melissa J. | Zendy; Takezaki Makoto | Zendy

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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.

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