Measurement of Solvation Ability of Solvents by Porphyrin-Based Solvation/Desolvation Indicators

Motonobu Sugimoto; Yusuke Kuramochi; Akiharu Satake

doi:10.1021/acsomega.9b04461

Measurement of Solvation Ability of Solvents by Porphyrin-Based Solvation/Desolvation Indicators

ACS Omega. 2020 Feb 18;5(11):6045-6050. doi: 10.1021/acsomega.9b04461. eCollection 2020 Mar 24.

Authors

Motonobu Sugimoto¹, Yusuke Kuramochi¹, Akiharu Satake¹

Affiliation

¹ Graduate School of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

Abstract

A new solvent scale, solvation ability (SA), was developed to arrange solvents in the order of their SA for large π-conjugated compounds. The SA of a solvent was determined in a binary solvent system of an assessed solvent and a standard "good" solvent (GS) or "poor" solvent (PS), chloroform or methylcyclohexane, respectively, in the presence of two types of solvation/desolvation indicators, 1Zn₂ and 2Zn₂ . The latter comprises bis(imidazolylporphyrinatozinc) linked via a 1,3-butadiynylene moiety having linear alkyl and hydrophilic side chains, respectively. GSs and PSs give extended (E-) and stacked (S-) supramolecular polymers of the indicators, respectively. SA values are defined as vol % of the standard solvent added to an assessed solvent to give the balance point where comparable amounts of E- and S-polymers of the indicators coexist. GSs and PSs have positive and negative signs, respectively. In this study, the SA of 25 solvents was determined. The SA values with indicator 1Zn₂ were as follows: ethyl acetate (-81), hexane (-66), toluene (-50), cyclohexane (-47), CCl₄ (-25), chloroform (50), and nitrobenzene (79).