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Microenvironments induced ring-closing of halide salt of oxazolidines: a rare inverse proton gradient process and its application in water-jet rewritable paper

Abstract

Proton gradient reactions are common, but the reaction with inverse proton gradient is rare. Inspired by the phenomenon that stomach can release acid initiatively when the inside microenvironment changes, an inverse proton gradient process along with a ring-closing of the precursors of oxazolidine molecular swiches (i.e. ROF+X-s) was achieved within specific microenvironments both in solution and on solid substrate. Nucleophilicity and concentration were found playing important roles in this process. Furthermore, benefitting from this inverse proton gradient generated ring-closing process, potential application of ROF+X-s instead of their akalization products—ring-closed forms (RCFs) of oxazolidines in water-jet rewritable paper (WJRP) was developed. Influences factors of dissolving solvent and drying temperature on hydrochromic performances of ROF+X- based WJRP were inspected and compared to its corresponding RCF based WJRP. Results indicate that the former outperforms the latter in color depth, coloration speed and retention time. The water-jet prints on ROF+X- based WJRP exert excellent legibility, resolution, uniformity, and repeatability. Success of this study not only will promote the industrialization of oxazolidines derivatives based WJRP for greatly reducing cost of production from a perspective of synthetic industrialization, but also might provide a reference for better understanding similar microenvironment-induced phenomena of inverse proton gradient in complex biosystems.

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Publication details

The article was received on 07 Jul 2018, accepted on 20 Aug 2018 and first published on 29 Aug 2018


Article type: Paper
DOI: 10.1039/C8TC03354D
Citation: J. Mater. Chem. C, 2018, Accepted Manuscript
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    Microenvironments induced ring-closing of halide salt of oxazolidines: a rare inverse proton gradient process and its application in water-jet rewritable paper

    G. Wenbin, T. Qin, G. Xi, L. Sheng and S. X. Zhang, J. Mater. Chem. C, 2018, Accepted Manuscript , DOI: 10.1039/C8TC03354D

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