25354-69-2Relevant academic research and scientific papers
Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives
Gunasekar, Ramachandran,Thamaraiselvi, Pichandi,Rathore, Ravindranath S.,Sathiyanarayanan, Kulathu Iyer,Easwaramoorthi, Shanmugam
, p. 12351 - 12358 (2015)
We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O?H-N-C=O?H-N?); i.e., dimers are linked through dimeric N-H?O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant π-π interactions. The 1H NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.
