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
{"title":"Synthesis of Fluorescent Diphenylanthracene-Based Calix[4]arene Derivatives and their Complexation with Alkali Metal Cations","authors":"M. Bakić, K. Leko, N. Cindro, T. Portada, T. Hrenar, Leo Frkanec, Gordan Horvat, J. Požar, V. Tomišić","doi":"10.5562/CCA3308","DOIUrl":null,"url":null,"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.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"711-725"},"PeriodicalIF":0.7000,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Croatica Chemica Acta","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.5562/CCA3308","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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.
查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
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.
期刊最新文献
Spectrophotometric Determination of N-acetyl-L-Cysteine in Pharmaceutical Formulations by Flow Injection and Sequential Injection Analysis: Comparison of the Methods Comparison of Radon Adsorption on Hematite and Charcoal Activated Powder in Air Synthesis, Experimental and Theoretical Characterization of (μ4-oxo)hexakis(μ2-chloro)-tetrakis[1-(allyl)-1H-imidazole]tetracopper(II) Ecofriendly Synthesis of DHPMs using Copper-based Nano catalysts and Evaluation of Antibacterial Activity Influence of Bitartrate Ion Concentration in the Copper Electrodeposition Onto a Polycrystalline Gold Electrode
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1