157671-41-5Relevant academic research and scientific papers
Solution and Solid-State Photochemistry of 2-Anilino-5-phenyl-2,4-pentadienenitriles
Liang, Yah-Long,Fang, Jim-Min,Chow, Tahsin,Ho, Tong-Ing,Lee, Chi-Rung,Wang, Yu
, p. 5742 - 5747 (1994)
2-(N-Methylanilino)-5-phenyl-2,4-pentadienenitrile (3) undergoes either isomerization or oxidative cleavage at the 2,3-double bond upon irradiation in solution, whereas it dimerizes in a regiospecific manner to give the cycloaddition product 12 upon irradiation in the solid state.From the fluorescence spectra and semiempirical calculations, the excited state of 3 is proposed to be a twist intramolecular charge transfer species.The X-ray analysis indicates that molecules of 3b orient appropriately with a reasonable distance for the cycloaddition in the solid state.The distance between C2 and C3' is 525 pm, the longest distance known in solid-state cycloadditions. 2-(N-Methyl-p-bromoanilino)-5-phenyl-2,4-pentadienenitrile (4) shows behavior similar to that of 3 in the solution and solid-state photochemistry, whereas analogs 7-10 having nitro substituents on the 5-phenyl rings do not dimerize upon irradiation in the solid state.Semiempirical calculation of the electronic structures is used to interprete the discrepancy of reactivity.
