Synthesis and spectroscopy of novel branched fluorescent dyes containing benzophenone parts and the possibility as fluorescence probes.
This paper describes a new fluorescent family of branched dyes containing benzophenone unit including 4-N, N-diphenylamino-4'-phenacyl-stilbene (C1), 4,4'-di(4-benzoylphenylethylene)yl-triphenylamine (C2) and 4,4',4″-tri(4-benzoylphenylethylene)yl-triphenylamine (C3). Benzophenone part is coupled with core through C-C double bond. The chemical structures of the derivatives are characterized with (1)H and (13)C nuclear magnetic resonance and elemental analysis. Strong π-π stacking interactions are discovered with the analysis of the X-ray crystallographic data of C1. The absorption maxima and emission maxima of the derivatives exhibit gradual bathochromic shift from C1 to C3. The optical density of C1, C2 and C3 are shown to be related to the number of branches. The changes of dipole moments between the excited and ground states for C1, C2 and C3 were estimated to be 4.356, 8.091 and 8.479 Derby, respectively by Lippert equation, confirming that the internal charge transfer (ICT) dominates the process of excited singlet state. The possibility as fluorescence probes of the derivatives on the estimation of what region of micelles interacting with samples was evaluated.
Gao
Fang
F
College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, China. fanggao1971@gmail.com
Niu
Lanying
L
Hu
Nvdan
N
Wang
Jianchao
J
Li
Hongru
H
Zhang
Shengtao
S
D001577:Benzophenones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D012996:Solutions; D013050:Spectrometry, Fluorescence / Q000379:methods*
D001577:Benzophenones; D005456:Fluorescent Dyes; D008823:Micelles; D012996:Solutions; C047723:benzophenone