Exploration of a new solvatochromic dye bearing the excited-state intramolecular proton transfer functionality

Moonjee Koh, Won Suk Kim, Minyung Lee

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

In an effort to explore a multifunctional dye, we investigated the spectroscopic properties of a benzofuran-based fluorophore, (E)-3-(6-(diethylamino) benzofuran-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DABP). We found that DABP shows a strong solvatrochromic effect in aprotic solvents and the excited-state intramolecular proton transfer (ESIPT) in protic solvents. We measured the fluorescence lifetime of DABP in different solvents and discovered that its lifetime decreases dramatically because of strong hydrogen bonding. One remarkable feature of the DABP emission is its high sensitivity to water content. We utilized this property to detect amyloid oligomers and observed that DABP is highly sensitive toward early-stage amyloid aggregates.

Original languageEnglish
Pages (from-to)556-560
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume37
Issue number4
DOIs
StatePublished - 1 Apr 2016

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea funded by the Ministry of Education (NRF-2013R1A1A2A10004510).

Publisher Copyright:
© 2016 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • Benzofuran
  • Charge transfer
  • DABP
  • Electron transfer
  • Solvatochromism

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