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Substituent Effect on the Spectra and Molecular Configuration of 3,4’-disubstituted Stilbene Derivatives

Author: LiuLiQiu
Tutor: CaoChenZhong
School: Hunan University of Science and Technology
Course: Organic Chemistry
Keywords: substituent effect stilbene derivatives UV spectra FL spectra crystal structure molecular configuration
CLC: O621.25
Type: Master's thesis
Year: 2009
Downloads: 37
Quote: 1
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Abstract


A series of 3,4’-substituted stilbenes were synthesized in this paper. their melting points were measured, and their molecular structures were confirmed by 1H NMR and 13C NMR. The UV spectra of the target compounds were mensurated in cyclohexane, ethyl ether and ethanol solvents, and FL spectra also were mensurated in ethanol. All mensurated data of the UV spectra and FL spectra were used to study the regulation of the substituent effect on the optical properties of the compound.The excited-state substituent constant was applied to research the UV spectra and FL spectra of 3,4’-substituted stilbenes. It was observed that the UV spectra and FL spectra data of 3,4’-substituted stilbenes have good correlations with excited-state substituent constant. Polar substituent constants, radical substituent constants and excited-state substituent constant were also employed to correlate with the the UV spectra and FL spectra of 3,4’-substituted stilbenes, respectively, and it was observed that the correlation of is better than that of polar substituent constants and radical substituent constants.A series of nitro-stilbene derivatives were synthesized with Wittig reaction of nitro-benzyltriphenylphosphonium salt and substituted benzaldehyde, in which the substituents including OMe, Cl, H, CN and NO2 were chosen. The target compounds were characterized by IR, UV,1H NMR,13C NMR and mass spectra. It was observed that the configuration of the stilbene derivatives depend on the substituents of the substituted benzaldehyde, in the case of that Wittig reactions of nitro-benzyltriphenylphosphonium salt and substituted benzaldehyde were carried out in CH2Cl2. The main products are the trans-stilbenes for the substituents OMe, Cl and H, and the cis-stilbenes for the substituents CN and NO2. The crystals of these nitro-stilbene derivatives were obtained by the solution method, and their crystal structures were determined by X-ray single crystal diffraction; The dihedral angles between the two benzene rings were determined and it was observed that:(ⅰ)all cis-stilbenes are in strongly nonplanar structures; (ⅱ)The trans-stilbene for the substituent OMe is in strongly nonplanar structure and the trans-stilbenes for the substituents Cl and H are in near-planar structures.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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