酰胺型二茂铁系金属有机色素三阶非线性光学材料合成研究
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摘要
二茂铁系金属有机三阶非线性光学材料是一类重要的有机光电功能材料,具有独特的电化学和光学特性,在光学信息处理、通讯和集成光学等高技术领域具有广泛的应用前景,是功能材料领域的一个研究热点。以酰胺基为桥基的二茂铁系金属有机色素三阶非线性光学材料目前报道不多,极具研究价值。
论文在查阅三阶非线性光学材料相关文献的基础上,对非线性光学效应及二茂铁系非线性光学材料合成、结构与性能关系等进行了综述,并设计合成了包含酰胺桥基、磺酰胺桥基的两大类共计14个二茂铁金属有机色素三阶非线性光学材料。
以二茂铁为原料,经Friedel-Crafts酰基化、氯仿反应、酰氯化、取代芳胺的N-酰化等一系列反应合成了9个具有A(D)-π-D-π-A(D)对称结构的二茂铁酰胺类金属有机三阶非线性光学材料,总收率在30%~49%之间,其中6个材料未见文献报道,材料经1H NMR和MS(ESI)表征确认。研究了Friedel-Crafts酰基化、氯仿反应、酰氯化反应和N-酰化反应的反应机理,确定了Friedel-Crafts酰基化反应条件为:乙酰氯为酰化试剂、无水三氯化铝为催化剂,收率77.8%。氯仿反应条件为:次氯酸钠为氧化剂,反应时间72h,收率72.4%。酰氯化反应条件为:草酰氯为酰氯化试剂,DMF为催化剂,收率90.7%。N-酰化反应条件为:二氯甲烷作溶剂,碳酸钠作缚酸剂,收率59~96%。
以二茂铁为原料,经磺化、酰氯化、与取代芳胺的N-酰化等一系列反应合成了5个具有D-π-A(D)结构的二茂铁磺酰胺类金属有机三阶非线性光学材料,总收率在6%~26%之间,其中1个材料未见文献报道,材料经1H NMR和MS(ESI)表征确认。研究了磺化反应和酰氯化反应的反应机理,确定了二茂铁磺酰氯的合成条件为:氯磺酸为磺化试剂,二氯甲烷为溶剂,反应时间48h,收率39.8%。N-酰化反应的收率为16%~66%。
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%.
论文在查阅三阶非线性光学材料相关文献的基础上,对非线性光学效应及二茂铁系非线性光学材料合成、结构与性能关系等进行了综述,并设计合成了包含酰胺桥基、磺酰胺桥基的两大类共计14个二茂铁金属有机色素三阶非线性光学材料。
以二茂铁为原料,经Friedel-Crafts酰基化、氯仿反应、酰氯化、取代芳胺的N-酰化等一系列反应合成了9个具有A(D)-π-D-π-A(D)对称结构的二茂铁酰胺类金属有机三阶非线性光学材料,总收率在30%~49%之间,其中6个材料未见文献报道,材料经1H NMR和MS(ESI)表征确认。研究了Friedel-Crafts酰基化、氯仿反应、酰氯化反应和N-酰化反应的反应机理,确定了Friedel-Crafts酰基化反应条件为:乙酰氯为酰化试剂、无水三氯化铝为催化剂,收率77.8%。氯仿反应条件为:次氯酸钠为氧化剂,反应时间72h,收率72.4%。酰氯化反应条件为:草酰氯为酰氯化试剂,DMF为催化剂,收率90.7%。N-酰化反应条件为:二氯甲烷作溶剂,碳酸钠作缚酸剂,收率59~96%。
以二茂铁为原料,经磺化、酰氯化、与取代芳胺的N-酰化等一系列反应合成了5个具有D-π-A(D)结构的二茂铁磺酰胺类金属有机三阶非线性光学材料,总收率在6%~26%之间,其中1个材料未见文献报道,材料经1H NMR和MS(ESI)表征确认。研究了磺化反应和酰氯化反应的反应机理,确定了二茂铁磺酰氯的合成条件为:氯磺酸为磺化试剂,二氯甲烷为溶剂,反应时间48h,收率39.8%。N-酰化反应的收率为16%~66%。
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%.
引文
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