Tuning Heterocalixarenes to Improve Their Anion Recognition: A Computational Approach

Alexandre O. Ortolan, Ina Østrøm, Giovanni F. Caramori*, Renato L.T. Parreira, Eder H. Da Silva, F. Matthias Bickelhaupt

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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We have explored and analyzed the physical factors through which noncovalent interactions in anion sensing based on calixarene-type hosts can be tuned, using dispersion-corrected DFT and Kohn-Sham molecular orbital (KS-MO) theory in conjunction with a canonical energy decomposition analysis (EDA). We find that the host-guest interaction can be enhanced through the introduction of strongly electron-withdrawing groups at particular positions of the arene and triazine units in the host molecule as well as by coordination of a metal complex to the arene and triazine rings. Our analyses reveal that the enhanced anion affinity is caused by increasing the electrostatic potential in the heterocalixarene cavities. This insight can be employed to further tune and improve their selectivity for chloride ions.

Original languageEnglish
Pages (from-to)3328-3336
Number of pages9
JournalJournal of Physical Chemistry A
Issue number12
Early online date15 Mar 2018
Publication statusPublished - 29 Mar 2018


A.O.O. thanks CNPq for his PhD scholarship (Grant 142339/ 2015-6). G.F.C. thanks CNPq (Grant 302408/2014-2) for the research fellowship. I.Ø. thanks CAPES for a Master’s scholarship (Grant 1732086). R.L.T.P. thanks FAPESP (Grant 2011/07623-8) and CAPES (Science without Borders program, Grant 88881.068346/2014-01) for financial support. F.M.B. thanks The Netherlands Organisation for Scientific Research (NWO) for financial support.

FundersFunder number
Fundação de Amparo à Pesquisa do Estado de São Paulo2011/07623-8, 88881.068346/2014-01
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior1732086
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Conselho Nacional de Desenvolvimento Científico e Tecnológico302408/2014-2, 142339/ 2015-6


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