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Porphyrin‐Based Molecular Rotors as Fluorescent Probes of Nanoscale Environments
Author(s) -
Ghiggino K. P.,
Hutchison J. A.,
Langford S. J.,
Latter M. J.,
Lee M. A. P.,
Lowenstern P. R.,
Scholes C.,
Takezaki M.,
Wilman B. E.
Publication year - 2007
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.200600948
Subject(s) - porphyrin , supramolecular chemistry , materials science , fluorescence , photoinduced electron transfer , quenching (fluorescence) , nanoscopic scale , photochemistry , viscosity , solvent , electron transfer , molecule , nanotechnology , organic chemistry , chemistry , optics , composite material , physics
The synthesis, characterization, and photophysical properties of a series of supramolecular triads consisting of a tin(IV) porphyrin with axial ligands of ortho ‐, meta ‐, and para ‐hydroxyphenyl naphthalenediimides are presented. For the meta ‐ and para ‐hydroxyphenyl derivatives, efficient and solvent‐viscosity‐dependent quenching of porphyrin fluorescence is observed. Experimental and theoretical studies demonstrate that, in these compounds, photoinduced electron transfer from the phenolate to the porphyrin is modulated by large amplitude rotational motions of the naphthalenediimide. These compounds are novel examples of fluorescent molecular rotors, and their potential use as environmental probes of local viscosity and temperature are discussed.