脱氢松香基有机小分子凝胶因子的合成及其性能

doi:10.3969/j.issn.0253-2417.2014.06.019

林产化学与工业 ›› 2014, Vol. 34 ›› Issue (6): 117-123.doi: 10.3969/j.issn.0253-2417.2014.06.019

脱氢松香基有机小分子凝胶因子的合成及其性能

童碧海¹, 张曼¹, 李剑飞², 马鹏¹, 王恒山², 张千峰¹

1. 安徽工业大学冶金与资源学院, 安徽马鞍山 243002;
2. 广西师范大学化学与药学学院, 广西桂林 541004

收稿日期:2013-10-28 出版日期:2014-12-25 发布日期:2015-08-18
通讯作者: 王恒山,博士生导师,研究领域为有机化学;E-mail:hshwang@mailbox.gxnu. E-mail:hshwang@mailbox.gxnu
作者简介:童碧海(1979-),男,湖南汉寿人,副教授,博士,主要从事光电功能材料的研究工作;E-mail:tongbihai@163.com
基金资助:
国家自然科学基金资助项目(81260472);广西自然科学基金重点资助项目(2011GXNSFD018010);安徽高校自然科学研究项目(KJ2013A063)

Synthesis and Properties of Organic Gelator Based on Dehydroabietate Derivative

TONG Bi-hai¹, ZHANG Man¹, LI Jian-fei², MA Peng¹, WANG Heng-shan², ZHANG Qian-feng¹

1. College of Metallurgy and Resources, Anhui University of Technology, Ma'anshan 243002, China;
2. School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China

Received:2013-10-28 Online:2014-12-25 Published:2015-08-18

摘要/Abstract

摘要： 用12-溴-13, 14-双硝基脱氢松香酸甲酯合成了一种新型的有机小分子凝胶因子1, 4a-二甲基-6-溴-1, 2, 3, 4, 4a, 17, 18, 18a-八氢萘基[2, 1-h] 二吡啶并[3, 2-a: 2, 3-c] 吩嗪甲酸甲酯(DBNPM),通过 ¹H NMR, ¹³C NMR, MS和IR等表征手段对产物结构进行了表征.为了考察此小分子凝胶因子的自组装行为,研究了该分子在不同有机溶剂中的成胶性能和形貌.研究发现,在甲醇中临界成胶浓度(C_GC)最低,为0.5 g/L;但是在二氧六环中凝胶性质最为稳定.扫描电镜(SEM)照片显示,从甲醇溶剂中得到的干胶呈片状结构,从二氧六环溶剂中得到的干胶呈网状结构;通过红外光谱和XRD测试研究证实,该化合物分子间的氢键是凝胶化的重要驱动力之一.

关键词: 脱氢松香酸甲酯, 有机小分子凝胶因子, 临界成胶浓度, 凝胶-溶胶相转变温度, 氢键

Abstract: A novel low-molecular-mass organic gelator (DBNPM) was synthesized from 12-bromine-13, 14-dinitro dehydroabietic acid methyl ester. The title compound was characterized by ¹H NMR, ¹³C NMR, IR and MS techniques. The assembly behavior of the prepared organogelator in solution was investigated. The organogelator induced gelation in a wide variety of organic solvents. With methanol as solvent, the critical gelation concentration (C_GC) of the prepared gelator was the minimum, 0.5 g/L. But the gelatination property was the most stable in 1, 4-dioxane. Scanning eletron microscope (SEM) images indicated that the xerogels from methanol solution presented flaky structure and the xerogels from 1, 4-dioxane solution were net-like structure. Infrared spectra (FT-IR) and XRD showed that hydrogen bond was the main driving force for the formation of organogels.

Key words: methyl dehydroabietate, low-molecular-mass organic gelators, critical gel concentration, gel-sol phase inversion temperature, hydrogen bond

中图分类号:

TQ351

童碧海, 张曼, 李剑飞, 马鹏, 王恒山, 张千峰. 脱氢松香基有机小分子凝胶因子的合成及其性能[J]. 林产化学与工业, 2014, 34(6): 117-123.

TONG Bi-hai, ZHANG Man, LI Jian-fei, MA Peng, WANG Heng-shan, ZHANG Qian-feng. Synthesis and Properties of Organic Gelator Based on Dehydroabietate Derivative[J]. Chemistry and Industry of Forest Products, 2014, 34(6): 117-123.

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脱氢松香基有机小分子凝胶因子的合成及其性能

Synthesis and Properties of Organic Gelator Based on Dehydroabietate Derivative

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