Bright, fluorescent dyes based on imidazo[1,2-a]pyridines that are capable of two-photon absorption

Dikhi Firmansyah , Adina I. Ciuciu , Vincent Hugues , Mireille Blanchard-Desce , Lucia Flamigni , Danielc T. Gryko

Abstract

A library of imidazo[1,2-a]pyridines was synthesized by using the Gevorgyan method and their linear and non-linear optical properties were studied. Derivatives that contained both electron-donating and electron-withdrawing groups at the 2 position were comprehensively investigated. Their emission quantum yield ranged between 0.2–0.7 and it was shown to depend on the substitution pattern, most notably that on the phenyl ring. Electron-donating substituents improved the luminescence performance of these compounds, whereas electron-withdrawing substituents led to a more erratic behavior. Substitution on the six-membered ring had less effect on the fluorescence properties. Extension of the delocalization increased the luminescence quantum yield. A new quadrupolar system was designed that contained two imidazo[1,2-a]pyridine units on its periphery and a 1,4-dicyanobenzene unit at its center. This system exhibited a large Stokes-shifted luminescence that was affected by the polarity and rigidity of the solvent, which was ascribed to emission from an excited state with strong charge-transfer character. This quadrupolar feature also led to an acceptable two-photon absorption response in the NIR region.
Author Dikhi Firmansyah (FC / DOC)
Dikhi Firmansyah,,
- Department Of Organic Chemistry
, Adina I. Ciuciu
Adina I. Ciuciu,,
-
, Vincent Hugues
Vincent Hugues,,
-
, Mireille Blanchard-Desce
Mireille Blanchard-Desce,,
-
, Lucia Flamigni
Lucia Flamigni,,
-
, Danielc T. Gryko (FC / DOC)
Danielc T. Gryko,,
- Department Of Organic Chemistry
Journal seriesChemistry-An Asian Journal, ISSN 1861-4728, [1861-471X]
Issue year2013
Vol8
No6
Pages1279-1294
Publication size in sheets0.75
Keywords in Englishdyes, fluorescence, nitrogen heterocycles, substituent effects, two-photon absorption
DOIDOI:10.1002/asia.201300058
URL http://onlinelibrary.wiley.com/doi/10.1002/asia.201300058/abstract
Languageen angielski
Score (nominal)35
ScoreMinisterial score = 35.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2013 = 3.935 (2) - 2013=4.147 (5)
Citation count*24 (2016-05-20)
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