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Study on the Synthesis of Amide-Containing Ferrocenyl Organometallic Chromophore Third-order Nonlinear Optical Materials

Author: TaoXiaoMin
Tutor: GaoJianRong；JiaJianHong
School: Zhejiang University of Technology
Course: Organic Chemistry
Keywords: amide ferrocene derivatives organometallic compound nonlinear optics synthesis
CLC: O627.81
Type: Master's thesis
Year: 2011
Downloads: 46
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Abstract


Ferrocenyl organometallic third-order nonlinear optical materials are an important class of organic photoelectric materials. Due to their unique electrochemical and optical properties, and their potential applications in optical information processing, communications, integrated optics and other high-tech fields, they have became a research priority in functional materials. Ferrocenyl organometallic third-order nonlinear optical materials with amide bridge are rarely reported, and have a great research value.Based on the retrieval of literatures, the syntheses and relationship between structure and properties of ferrocenyl organometallic third-order nonlinear optical material and the nonlinear optical effect were comprehensively reviewed; A series of 14 ferrocenyl organometallic third-order nonlinear optical materials with amide or sulfonamide bridge were synthesized in the dissertation. A series of 9 amide-containing ferrocenyl organometallic third-order nonlinear optical materials with A(D)-π-D-π-A(D) symmetrical structures were synthesized via Friedel-Crafts acylation, haloform reaction, acyl chlorination and N-acylation. The total yields were reached from 30% to 49%. The structure of the material was confirmed by 1H NMR and MS. The mechanism of Friedel-Crafts acylation, haloform reaction, acyl chlorination were investigated. The optimal parameters of Friedel-Crafts acylation were selected as follows:acetyl chloride as acylating reagent, anhydrous aluminum chloride as catalyst, the yield was 77.8%. The optimal parameters of haloform reaction were selected as follows:sodium hypochlorite as oxidant, the reaction time was 72h, the yield was 72.4%. The optimal parameters of acyl chlorination were selected as follows:oxalyl chloride as acyl chloride reagent, DMF as catalyst, the yield was 90.7%. The optimal parameters of N-acylation were selected as follows:CH2Cl2 as solvent , sodium carbonate as acid binding agent, the yields were reached from 59% to 96%.A series of 5 sulfonamide-containing ferrocenyl organometallic third-order nonlinear optical materials with D-π-A(D) asymmetric structures were synthesized via sulfonation, acyl chlorination and N-acylation. The total yields were reached from 6% to 26%. The structure of the material was confirmed by 1H NMR and MS. The mechanism of sulfonation, acyl chlorination were investigated. The optimal parameters of ferrocenesulfonyl chloride were selected as follows:Chlorosulfonic acid as sulfonation reagent, CH2Cl2 as solvent, the reaction time was 48h, the yield was 39.8%. The yields of N-acylation were reached from 16% to 66%.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds > Ⅷ of group elements, organic compounds > Iron organic compounds
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