Synthesis and Photophysical Investigation of a Series of Push–Pull Arylvinyldiazine Chromophores

Abstract

A new series of push-pull arylvinyldiazines has been efficiently prepared by aldol condensation between the appropriate methyldiazine and aromatic aldehyde. The optical absorption and emission properties of these chromophores were studied in different solvents and media. These compounds act as polarity sensors with a strong positive emission solvatochromism. This behavior suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. These molecules also exhibit halochromic properties and are potential colorimetric and luminescence pH sensors. The second-order nonlinear properties have been investigated for some of the compounds, and large and positive μβ are obtained, in particular, for pyrimidine derivatives.

2-Arylvinylpyrimidines versus 4-arylvinylpyrimidines: synthesis and comparison of the optical properties

“…Such phenomena has been already observed with arylvinyldiazine substituted with amino groups. 8,16 It should be noted that the same blue shift is not observed for compounds 5c and 5e. In an effort to gain further insight into the photophysical process within these pushpull molecules, we investigated the emission behaviors of compounds 5 and 6 in different aprotic solvents.…”

“…5 Recently we have also described 4-arylvinylpyrimidines that can be used as metal cation sensors, 6 duplex DNA sensors 7 and second order NLO chromophores. 8 Even if some 2-arylvinylpyrimidines have been described for their biological activities, 9 to the best of our knowledge, the photophysical properties of these derivatives have not been studied.…”

Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

“…Moreover, it should be noted that arylvinyl pyrimidines are now considered as well established structures of two-photon absorption dyes [26][27][28]. Some pyrimidine derivatives exhibit also the second order nonlinear optical properties [28][29][30][31].…”

Synthesis of Pyridazine Derivatives by Suzuki-Miyaura Cross-Coupling Reaction and Evaluation of Their Optical and Electronic Properties through Experimental and Theoretical Studies

“…Recently, research targeting molecules based on pyridazine heterocycles has grown considerably due to their numerous applications as therapeutic agents [8,9], chemiluminescent materials [10,11,12], ligands for heterogeneous catalysis [13,14], in supramolecular chemistry [15], and nonlinear optical [16,17,18,19,20,21,22,23,24] and photovoltaic materials [25]. This wide array of interesting applications has motivated the development of procedures for the preparation of differently substituted pyridazines.…”

“…Whereas several series of pyridazine derivatives have been reported as efficient two-photon absorption (TPA) fluorophores [18,20,23], studies describing nonlinear optics (NLO) second harmonic generation properties (SHG) remain limited to a restricted number of compounds [16,19,21,22,24], which included organometallic compounds bearing pyridazine ligands [21]. Furthermore, it is noteworthy fact that none of these publications report the synthesis and evaluation of SHG pyridazine NLOphores constituted by pyridazine and thiophene heterocyclic moieties, which act simultaneously as π-bridge and auxiliary electron acceptor or electron donor groups, respectively.…”