Synthesis and spectral properties of new fluorescent alkoxy-substituted thieno[3,2-b]indole derivatives
Cheikh Lo1, Baba Issa Doucoure2, Jean-Jacques Aaron3
1Laboratoire Géomatériaux et Environnement (LGE), EA 4508, Université Paris-Est-Marne-la-Vallée (UPEMLV), 5 boulevard Descartes, Champs-sur-Marne, 77454 Marne-la-Vallée Cedex 2, France; Département de Chimie, Faculté des Sciences et Techniques, Université C.A. Diop, Dakar, Senegal.
Abstract:
The synthesis and optical properties of three new fluorescent alkoxy-substituted thieno[3,2-b]indole (TI) derivatives, including 7-methoxy thieno[3,2-b]indole (7-MeOTI), 6,7- methylenedioxythieno[3,2-b]indole (6,7-MDTI) and 6,7-dihexyloxythieno[3,2-b]indole, (6,7-DHTI), were investigated. Electronic absorption spectra, fluorescence excitation and emission spectra, fluorescence quantum yields (ΦF), lifetimes (τF), and other photophysical parameters of the three TI derivatives were measured in DMSO solutions at room temperature. Theoretical electronic absorption and fluorescence spectra were also calculated by means of a molecular orbital (MO) method. For all three alkoxy-TI derivatives, the fluorescence emission maximum wavelength was significantly red shifted relative to un-substituted TI, which was attributed to delocalization of the fused hetero-aromatic ring π electronic system by the electron-donating alkoxy group(s). ΦF values varied from 0.12 to 0.19, according to the compound. τF were short, in the range 0.56-1.13 ns.
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