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Heterocyclic Quinol‐Type Fluorophores: Synthesis, X‐ray Crystal Structures, and Solid‐State Photophysical Properties of Novel 5‐Hydroxy‐5‐substituent‐benzo[ b ]naphtho[1,2‐ d ]furan‐6‐one and 3‐Hydroxy‐3‐substituent‐benzo[ kl ]xanthen‐2‐one Derivatives
Author(s) -
Ooyama Yousuke,
Okamoto Tomohiro,
Yamaguchi Takahiro,
Suzuki Toshihisa,
Hayashi Akiko,
Yoshida Katsuhira
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600094
Subject(s) - fluorescence , chromophore , substituent , chemistry , crystal structure , photochemistry , crystallography , solid state , absorption (acoustics) , crystal (programming language) , absorption spectroscopy , emission spectrum , spectral line , stereochemistry , materials science , physics , quantum mechanics , computer science , programming language , composite material , astronomy
Novel heterocyclic quinol‐type fluorophores ( 4 a – c ) and ( 5 a – c ) that contain substituents (R = Me, Bu, Ph) with nonconjugated linkages to the chromophore skeleton have been synthesized and their photophysical properties have been investigated in solution and in the solid state. Considerable differences in the absorption and fluorescence spectra were observed between the two states. Quinols 4 a – c and 5 a – c exhibited almost the same absorption and fluorescence spectra in solution; however, their solid‐state fluorescence excitation and emission spectra in the crystalline state were quite different. We performed X‐ray crystallographic analyses to elucidate the dramatic effect of the substituents of the nonconjugated linkage on the solid‐state fluorescence excitation and emission spectra. The relationships between the solid‐state photophysical properties and the chemical and crystal structures of 4 a – c and 5 a – c are discussed on the basis of the X‐ray crystal structures.