Synthesis, fluorescence properties, and conformational analysis of ether-linked (1,8)pyrenophanes

TETRAHEDRON

卷:75

Article

Maeda, Hajime¹  Geshi, Makoto¹  Hirose, Kenji¹  Furuyamaa, Taniyuki^1,2  Segi, Masahito¹ 

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Chem, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

[2] Japan Sci & Technol Agcy JST PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan

关键词: Cyclophane;    Pyrene;    Pyrenophane;    Fluorescence;    Excimer;   

DOI  :  10.1016/j.tet.2019.130512

来源: Elsevier

【 摘 要 】

Mono-, di- and oligo-ether linked (1,8)pyrenophanes 1-7 were synthesized, and their fluorescence and conformational properties in the absence and presence of metal ions were elucidated. Fluorescence spectra of 1.0 x 10(-5) M solutions of the mono- and di-ether linked pyrenophanes 1-5 were comprised of only monomer emission bands, while those of the oligoethylene glycol linked analogs 6 and 7 contained both monomer and intramolecular excimer emission bands. Addition of perchlorate salts of Ba2+, Na+ and Li+ to 1:1 v/v CH3CN:CH2Cl2 solutions of 6 and 7 caused decreases in the intensities of the corresponding intramolecular excimer emission bands and, in some cases, increases in the intensities of the monomer emission. Monomer and intramolecular excimer emission from the (1,8)pyrenophanes are suggested to arise from the respective anti and syn conformers, whose ratios are dependent on solvent polarity, temperature and kinds of added metal ions. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

Free