Solvatochromism, anion binding and electrochemistry in 5,15-porphodimethenes

Synthesis and characterization of substituted 5,15-bis-(4′-hydroxy-3′,5′-di-tert-butyl-phenyl)-porphodimethenes (3a-b), are described. Spectroscopic studies of redox-active 3,5-di-tert-butyl-4-hydroxyphenyl substituted porphodimethene 3a, 3b reveal a change in conformation via acid/base-switched tau...

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Bibliographic Details
Published inDyes and pigments Vol. 142; pp. 262 - 271
Main Authors Nagpal, Ritika, Arora, Smriti, Rawat, Amit Kumar, Ponnan, Prija, Chauhan, Shive M.S.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.07.2017
Subjects
Hydroxyporphodimethenes
Receptors
Sensing
Solvatochromism
Solvatochromism
Sensing
Receptors
Hydroxyporphodimethenes
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Summary:Synthesis and characterization of substituted 5,15-bis-(4′-hydroxy-3′,5′-di-tert-butyl-phenyl)-porphodimethenes (3a-b), are described. Spectroscopic studies of redox-active 3,5-di-tert-butyl-4-hydroxyphenyl substituted porphodimethene 3a, 3b reveal a change in conformation via acid/base-switched tautomerism by simultaneously switching between porphodimethene and porphyrinogen accompanied by visible chromogenic changes. The novel prototype exhibits a positive solvatochromism and chromogenically senses fluoride (specifically in polar solvents) and hydroxide ion (in all solvents). The unique structural changes along with distinct color changes were monitored by UV–Vis, fluorescence, cyclic voltammetry NMR spectroscopic techniques and DFT computations. [Display omitted] •Excellent positive absorption solvatochromism.•The porphodimethenes display remarkable colorimetric response towards OH− and F− ions.•The colorimetric chemosensor acts as potential probe towards polar solvents.•Tautomeric behaviour is responsible for the observed color change and anion binding.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2017.03.027