芳香寡聚磺酸酯桥联大环化合物的合成和紫外光谱

doi:10.11944/j.issn.1000-0518.2015.03.140231

摘要/Abstract

摘要：

以芳香二磺酰氯和芳香二酚为原料,三乙胺作缚酸剂,二氯甲烷作溶剂,采取一步成环法合成了一系列新型的、芳环单元不同的芳香寡聚磺酸酯桥联大环化合物。合成产物的结构用IR、¹H NMR、¹³C NMR和MALDI-TOF等技术手段进行了确认。并对合成方法、紫外光谱和变温核磁结构研究进行了有价值的探讨。化合物3~5的DMF溶液的最大紫外吸收峰在266 nm处,化合物6在267 nm处,摩尔吸光系数分别是4.65×10⁴、5.61×10⁴、5.09×10⁴和9.98×10⁴ L/(mol·cm);检出限分别是2.15×10^-7、1.78×10^-7、1.96×10^-7和1.00×10^-7 mol/L。变温核磁数据证明,苯环上连有支链有利于固定构象,可以通过这种方法合成结构固定的杯芳烃。

关键词: 大环化合物, 磺酸酯, 合成, 变温核磁, 紫外光谱

Abstract:

A series of aromatic oligosulfonate-bridged macrocyclic compounds was synthesized using aromatic disulfonyl chlorides and aromatic diphenol as the starting materials. The products were characterized by IR, ¹H NMR,¹³C NMR and MALDI-TOF-MS. The synthetic methods, UV spectra and variable-temperature ¹H NMR experiments were also discussed herein. UV spectra maximum absorption peaks of compounds 3~5 and compound 6 in DMF solutions are at 266 nm and 267 nm, respectively. The molar absorption coefficients are 4.65×10⁴, 5.61×10⁴, 5.09×10⁴ and 9.98×10⁴ L/(mol·cm), respectively. The detection limits are 2.15×10^-7, 1.78×10^-7, 1.96×10^-7 and 1.00×10^-7 mol/L, respectively. Variable-temperature ¹H NMR experiments show that branched benzene rings can lock the conformation and facilitate the synthesis of desired macrocylces.

Key words: macrocyclic compound, sulfonate, synthesis, variable-temperature 1H NMR, UV spectra

中图分类号:

张德春, 王文革, 孙爱明, 刘开建, 欧丽娟, 李爱阳. 芳香寡聚磺酸酯桥联大环化合物的合成和紫外光谱[J]. 应用化学, 2015, 32(3): 292-298.

ZHANG Dechun, WANG Wen'ge, SUN Aiming, LIU Kaijian, OU Lijuan, LI Aiyang. Synthesis and UV Spectra of Aromatic Oligosulfonate-bridged Macrocycles[J]. Chinese Journal of Applied Chemistry, 2015, 32(3): 292-298.

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