An acrylated isocyanonaphthalene based solvatochromic click reagent: Optical and biolabeling properties and quantum chemical modeling

Miklós Nagy, Dávid Rácz, Zsolt László Nagy, Tibor Nagy, Péter Pál Fehér, Mihály Purgel, M. Zsuga, S. Kéki

Research output: Article

6 Citations (Scopus)

Abstract

The optical and biolabeling properties of a novel molecule 1-(2-acryloyloxy-3-chloro-prop-1-yl)-amino-5-isocyanonaphthalene (ACAIN) is reported. In addition to being a real solvatochromic fluorophore it reacts quantitatively and rapidly with simple thiols in a thiol-ene click reaction. DFT calculations revealed a dark nonfluorescent state of ACAIN due to a close energy triplet state where electron transition can happen between the acrylic double bond and the aromatic core through an intramolecular hydrogen bond between the NH and [Formula presented] moieties. The hydrothiolation reaction is accompanied by a 1.5–19 fold increase in fluorescence intensity depending on the solvent used owing to the saturation of the acrylic group. The quantum yield and reactivity of the molecules were found to be largely dependent on the substituent of the acryl moiety. The biolabeling properties were investigated in detail by fluorometry and electrospray ionization (ESI) mass spectrometry using cysteine, KAC as a simple tripeptide and BSA as a model protein.

Original languageEnglish
Pages (from-to)445-457
Number of pages13
JournalDyes and Pigments
Volume133
DOIs
Publication statusPublished - okt. 1 2016

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Fingerprint Dive into the research topics of 'An acrylated isocyanonaphthalene based solvatochromic click reagent: Optical and biolabeling properties and quantum chemical modeling'. Together they form a unique fingerprint.

  • Cite this