TY - JOUR
T1 - Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state
AU - Yamaji, Minoru
AU - Okamoto, Hideki
N1 - Funding Information:
This work has been supported by a Grant-in-Aid for Scientific Research ( JP26288032 , JP17K0597621 and JP18H02043 ) from JSPS to MY and HO. MY acknowledges Prof. Fumito Tani and the technical staff at Kyushu University for performing the HRMS spectrometry of 2b under the Cooperative Research Program of Network Joint Research Center for Materials and Devices. MY is grateful to the association for the advancement of Science & Technology, Gunma University for financial support. Appendix A
Publisher Copyright:
© 2018 Elsevier B.V.
PY - 2018/6/1
Y1 - 2018/6/1
N2 - 1-Hydroxy-2-acetonaphthone, compound 1b is known to undergo excited-state intramolecular proton transfer (ESIPT) in the lowest excited singlet state in solution, giving weak fluorescence with a large Stokes-shift. We converted compound 1b to the corresponding difluoroboronated (BF2) complex 2b, and investigated the photophysical features in solution and the solid state along with those of the related compound 1d. The other compounds 1a, 1c and 1d were unsuccessful in forming the corresponding BF2 complexes. Blue fluorescence from compounds 1a, 1b and 1d and yellow one from compound 2b in the solid state were recorded. Compounds 1a, 1b and 1d moderately fluoresced with quantum yields of ca. 0.2 in both solution and solid state. Compound 2b showed fluorescence in the solid state with a quantum yield of 0.18 and in solution with a quantum yield of 0.65. The present study introduces potentials of ESIPT molecules, the related compounds and the corresponding difluoroboronated complexes to solid-state fluorophores.
AB - 1-Hydroxy-2-acetonaphthone, compound 1b is known to undergo excited-state intramolecular proton transfer (ESIPT) in the lowest excited singlet state in solution, giving weak fluorescence with a large Stokes-shift. We converted compound 1b to the corresponding difluoroboronated (BF2) complex 2b, and investigated the photophysical features in solution and the solid state along with those of the related compound 1d. The other compounds 1a, 1c and 1d were unsuccessful in forming the corresponding BF2 complexes. Blue fluorescence from compounds 1a, 1b and 1d and yellow one from compound 2b in the solid state were recorded. Compounds 1a, 1b and 1d moderately fluoresced with quantum yields of ca. 0.2 in both solution and solid state. Compound 2b showed fluorescence in the solid state with a quantum yield of 0.18 and in solution with a quantum yield of 0.65. The present study introduces potentials of ESIPT molecules, the related compounds and the corresponding difluoroboronated complexes to solid-state fluorophores.
KW - Difluoroboron complex
KW - ESIPT
KW - Fluorescence lifetime
KW - Fluorescence quantum yield
KW - Solid-state fluorescence
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U2 - 10.1016/j.jphotochem.2018.04.017
DO - 10.1016/j.jphotochem.2018.04.017
M3 - Article
AN - SCOPUS:85046796311
VL - 360
SP - 204
EP - 209
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
ER -