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Synthesis, Crystal Structure, Spectral and Thermodynamic Properties of One Benzoindole Pentamethine Cyanine Dye
Author(s) -
Zhang XiuFu,
Zhao JunLong,
Bi WeiBin,
Zhang DanDan,
Yang ZhiYuan,
Wang LanYing
Publication year - 2013
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201200405
Subject(s) - chemistry , cyanine , dimer , hydrogen bond , aqueous solution , enthalpy , orthorhombic crystal system , monomer , intermolecular force , chloroform , absorption spectroscopy , crystallography , methanol , fluorescence , photochemistry , crystal structure , molecule , organic chemistry , polymer , physics , quantum mechanics
One benzoindole pentamethine cyanine dye was synthesized and characterized by 1 H NMR, IR, MS and UV‐Vis spectra. The UV‐Vis absorption and fluorescence spectra of the dye in chloroform, dimethyl sulfoxide, acetone, ethanol and methanol were investigated, and the λ max of the dye was in the region 682.0–689.0 nm with large molar extinction coefficients (ϵ > 10 5 M −1 cm −1 ) in different solvents. The structure of the dye was also characterized and analyzed by X‐ray diffraction. Crystallographic data revealed that the dye belonged to orthorhombic, with space group P2 1 2 1 2 1 , a = 10.059(2) Å, b = 15.098(4) Å, c = 24.989(6) Å, V = 3794.8(15) Å 3 , Z = 4. The C‐H···F intermolecular hydrogen bonds were displayed in the molecular system, which were effective in the molecular packing. The aggregation behavior and thermodynamic properties of the dye in aqueous methanol solution were also studied by means of UV‐Vis spectroscopy methods. The results indicated that the dye existed monomer‐dimer equilibrium in aqueous methanol solutions. The fundamental properties of the dye, such as the dimeric association constant K D , the dimeric free energy Δ G D , the dimeric entropy Δ S D , and the dimeric enthalpy Δ H D were determined. The Δ H D of the dye was –46.0 kJ mol −1 .