Synthesis and spectroscopic characterization of Y-shaped fluorophores with an imidazole core containing crown ether moieties

Dogru U., ÖZTÜRK ÜRÜT G., Bayramin D.

JOURNAL OF LUMINESCENCE, cilt.163, ss.32-39, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 163
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.jlumin.2015.03.001
  • Dergi Adı: JOURNAL OF LUMINESCENCE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.32-39
  • Anahtar Kelimeler: Imidazole, Y-shaped molecules, Crown ether, 15-Crown-5, 2-PHOTON ACTIVE FLUOROPHORE, FLUORESCENT SENSOR, DERIVATIVES, ABSORPTION, PARAMETERS, LIGANDS
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

In this study three new Y-shaped fluorophores, 4,5-(2,2'-diphenyl)vinyl-{2-[(1,4,7,10-tetraoxa-13-azacyclopentadecyl)phenyl]}-1H-imidazole (1a), 4,5{[2,2'-bis(4-methoxyphenyl)vinyl]-[2-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)-phenyl])-1H-imidazole (1b) and 4,5-(2,2'-diphenyl)vinyl-{2-(1,4,7,10,13-benzopentaoxacyclopentadecyl))-1H-imidazole (1c) were synthesized. 1,6-Diphenylhexa-1,5-diene-3,4-dione (2a) and 1,6-bis(4-methoxyphenyl)hexa-1,5-diene-3,4-dione (2b) were synthesized as preliminary fluorophores and then reacted with 4-formylbenzo-aza-15-crown-5 (3a) and 4-formylbenzo-15-crown-5 (3b) to obtain the three Y-shaped fluorophores 1a, 1b and 1c. 4-formylbenzo-aza-15-crown-5 and 4-formylbenzo-15-crown-5 intermediates were synthesized with Vilsmeier-Haack reaction. The photophysical properties such as maximum absorption wavelengths, maximum emission wavelengths, Stokes shifts, singlet energies, fluorescence quantum yields and photostabilities of the compounds were investigated by measuring absorption and emission spectra in a series of solvents of varying polarities of toluene (TOL), dichloromethane (DCM), tetrahydrofuran (THF), ethyl acetate (EA), acetonitrile (ACN), and N,N-dimethylformamide (DMF). The three compounds 1a, 1b and 1c exhibited emission maxima in the 412-677 nm range. All the derivatives synthesized exhibited excellent photostability in all the solvents tested. (C) 2015 Elsevier B.V. All rights reserved.