Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate

Abstract

Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro[chromene-2,2′-indoline]-6-carboxylate, was obtained via the cyclocondensation reaction from 5-chloro-1,2,3,3-tetramethyl-3H-indolium perchlorate and methyl 3,5-diformyl-2,4-dihydroxy-benzoate. The molecular structure of the target compound was confirmed by 1H, 13C NMR, and IR spectroscopy, as well as LC/MS and elemental analysis. Photochemical studies revealed photochromic activity for the obtained spiropyran at room temperature. The photoinduced merocyanine form demonstrated an enhanced lifetime and fluorescent properties in the red region of the spectrum.

Keywords

• spiropyran
• photochromism
• molecular switch
• indoline
• heterocycles
• polyfunctional substituents