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
AbstractA 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.
|Journal series||Chemistry-An Asian Journal, ISSN 1861-4728, [1861-471X]|
|Publication size in sheets||0.75|
|Keywords in English||dyes, fluorescence, nitrogen heterocycles, substituent effects, two-photon absorption|
|Score|| = 35.0, 28-11-2017, ArticleFromJournal|
= 35.0, 28-11-2017, ArticleFromJournal
|Publication indicators||: 2013 = 3.935 (2) - 2013=4.147 (5)|
|Citation count*||24 (2016-05-20)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.