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Preparation of a family of 10-hydroxybenzo[h]quinoline analogues via a modified Sanford reaction and their excited state intramolecular proton transfer properties.
This synthesis was compatible with diverse functionalities and worked for sterically hindered analogues as well as for compounds possessing electron-donating and electron-withdrawing substituents at various positions, and demonstrated excited-state intramolecular proton transfer (ESIPT). Expand
Strongly emitting fluorophores based on 1-azaperylene scaffold.
A novel blue-emitting polycyclic aromatic system was synthesized via anion-radical coupling that led to a phenol possessing an intramolecular hydrogen-bond system through efficient direct hydroxylation. Expand
12-hydroxy-1-azaperylene-limiting case of the ESIPT system: enol-keto tautomerization in S0 and S1 states.
Observation of absorption and fluorescence of both tautomeric forms and lack of large Stokes shift offluorescence of the keto form classify HAP as the limiting case of the excited-state intramolecular proton transfer system. Expand
Synthesis and properties of directly linked corrole–ferrocene systems
Meso-substituted corroles bearing directly linked ferrocene unit have been synthesized for the first time. Among various methods studied, only the condensation of pentafluorophenyldipyrromethane withExpand
Excited state intramolecular proton transfer in electron-rich and electron-poor derivatives of 10-hydroxybenzo[h]quinoline.
On the basis of time-resolved measurements, proton transfer was found to be extremely fast with time constants in the range (0.08-0.45 ps) and some design patterns giving rise to NIR emission and large Stokes shifts were identified. Expand
Excited state intramolecular proton transfer in π-expanded phenazine-derived phenols.
Two previously inaccessible analogs of 10-hydroxybenzo[h]quinoline were prepared via a straightforward strategy comprising the formation of π-expanded phenazines skeleton followed by C-H acetoxylation at position 10 and these phenazine analogues constitute one of largest heterocycles for which ESIPT was unambiguously detected. Expand
Low-temperature spectra of the analogues of 10-hydroxybenzo[h]quinoline as an indication of barrierless ESIPT.
The π-expansion of the 10-HBQ chromophore led to compounds possessing diverse photophysical properties, ranging from the non-ESIPT strongly fluorescent molecule of 10-hydroxy-1-azaperylene to weakly emitting (or nonemitting) molecules, where ESIPT occurs very efficiently. Expand
From bifunctional nucleophilic behavior of DBU to a new heterocyclic fluorescent platform.
An unexpected discovery of a novel cyclocondensation reaction of 1,8-diazabicyclo-undec-8-ene (DBU) with activated 1,2-dichloro compounds is described, which generates the 2-aminopyrrole skeleton. Expand
Azine-imidazole aza -BODIPY analogues with large Stokes shift
Abstract A series of azine-imidazole aza-BODIPY analogues has been prepared by a simple synthesis from 2-azinecarboxylic acids and imidazole N-oxides. The new fluorescent complexes exhibit largeExpand
Fluorescent Dyes with 2-Amino-4,7-diazaindole Skeleton : Synthesis and Spectroscopy
The reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with compounds possessing two vicinal chlorine atoms activated toward nucleophilic substitution has been studied. All derivatives bearing a ...