Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials

Elisabete Oliveira , Rosa M. F. Baptista, Susana P. G. Costa, M. Manuela M. Raposo, Carlos Lodeiro

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The demand for dyes with solvatochromic properties has increased in the last few years, mainly due totheir wide range of applications in the analytical and industrial fields, such as in the textile industry. Thephenomenon of solvatochromism is associated with the differential solvation of the ground and excitedstates of the solvatochromic compounds, leading to an important tool for the study of the natureof solute–solvent interactions. In this paper we report the synthesis of new bis(indolyl)methanederivatives bearing arylthiophene spacers (2a–d) functionalized with electron-donating and electronwithdrawinggroups, and the photophysical studies in different solvents, such as ethanol, acetonitrile,dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to exploretheir solvatochromic behaviour in the ground and excited states, all solvents employed have differenthydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, thesolution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane andpurple in 1,4-dioxane. A negative solvatochromism was observed in 2b and a positive one in 2a, 2c and 2d.
Original languageEnglish
Pages (from-to)492-498
Number of pages7
JournalPhotochemical and Photobiological Sciences
Volume13
Issue number3
DOIs
Publication statusPublished - 2014

Keywords

  • PHENOLATE BETAINE DYES
  • STATE DIPOLE-MOMENTS
  • LIQUID-CHROMATOGRAPHY
  • SOLVENT POLARITIES
  • POLYAMINES
  • VALUES
  • PHASE
  • SCALE
  • PH

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