Synthesis of Fluorescent Diphenylanthracene-Based Calix[4]arene Derivatives and their Complexation with Alkali Metal Cations

IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Croatica Chemica Acta Pub Date : 2017-12-29 DOI:10.5562/CCA3308
M. Bakić, K. Leko, N. Cindro, T. Portada, T. Hrenar, Leo Frkanec, Gordan Horvat, J. Požar, V. Tomišić
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引用次数: 1

Abstract

Two novel fluorescent calix[4]arenes comprising diphenylanthracene moiety at the lower rim were synthetized and their complexation with alkali metal cations in acetonitrile/dichloromethane and methanol/dichloromethane mixtures (φ = 0.5) was studied experimentally and by classical molecular dynamics and quantum chemical calculations. The monosubstituted calixarene derivative (L1) proved to be a poor cation receptor, whereas the ester-based macrocycle (L2) exhibited rather high affinity towards lithium, sodium and potassium cations, particularly in MeCN/CH2Cl2. All complexation reactions were enthalpically controlled, whereby the overall stability was the largest in the case of sodium complex. The computational investigations provided an additional insight into the complexation properties and structures of complex species. The molecular dynamics simulations indicated the occurrence of inclusion of solvent molecules in the calixarene hydrophobic cavity of the free and complexed ligand, which was found to significantly affect the complexation equilibria.
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荧光二苯基蒽基杯[4]芳烃衍生物的合成及其与碱金属阳离子的络合反应
合成了两种新的荧光杯[4]芳烃,并通过经典分子动力学和量子化学计算,研究了它们与乙腈/二氯甲烷和甲醇/二氯甲烷混合物(φ=0.5)中碱金属阳离子的络合反应。单取代杯芳烃衍生物(L1)被证明是较差的阳离子受体,而基于酯的大环(L2)对锂、钠和钾阳离子表现出相当高的亲和力,特别是在MeCN/CH2Cl2中。所有的络合反应都受到焓控制,从而在钠络合物的情况下总体稳定性最大。计算研究为复杂物种的络合性质和结构提供了额外的见解。分子动力学模拟表明,溶剂分子出现在游离和络合配体的杯芳烃疏水腔中,这显著影响络合平衡。
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来源期刊
Croatica Chemica Acta
Croatica Chemica Acta 化学-化学综合
CiteScore
0.60
自引率
0.00%
发文量
3
审稿时长
18 months
期刊介绍: Croatica Chemica Acta (Croat. Chem. Acta, CCA), is an international journal of the Croatian Chemical Society publishing scientific articles of general interest to chemistry.
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