The effect of the supramolecular network of (Z)-3-(4-(diphenylamino)phenyl)-2-(pyridin-2-yl)-acrylonitrile on the fluorescence behavior of a single crystal: experimental and theoretical studies

Abstract

The molecular structure, molecular interactions, self-assembly behaviour and optical properties of a α,β-unsaturated nitrile were analyzed.

Preferential Orientation of Crystals and its Influence on the Emission Wavelength of Acrylonitrile Derivatives Treated with Polar Solvents

“…Table includes a list of selected bond lengths and torsion angles for III–V . The p ‐diphenylamino substituent prevents a delocalization on the central part of the molecular structure formed by the phenyl ring attached to the acrylonitrile moiety, and consequently, the molecular packing is disturbed by intermolecular interaction. The double bond lengths of C(19)–C(20) [1.352(2) for III , 1.351(2) and 1.352(2) for IV , 1.351(2) for V ] are identical in all three structures.…”

“…The contact distances between molecules can be affected by any, all, or none of these three strains ( Figure ). The conformer A has been typically found in different isomeric compounds that have been crystallized . The IV torsion angles between molecules A and B have values that are closer, within the standard uncertainties (Table S2, Supporting Information), indicating that crystal packing between A and B conferred a twist on the acrylonitrile group, making the phenylacrylonitrile moiety almost planar.…”

“…The one photon absorption spectra in the UV spectra of each pair of crystals (yellow and orange) dissolved in CHCl 3 or in CH 2 Cl 2 showed two absorption bands: one at λ max 296–301 nm, corresponding to the n→π* transition due to electron transfer from the amine moieties and a second absorption band with λ max at 416–427 nm, which is assigned to π–π* transition of the conjugated double bond . The presence of the substituents, either the N(CH 3 ) 2 or ‐N(Ph) 2 group, increased the intensity of the bands assigned to n→π*, which corresponded to the extended delocalization of the nitrogen pair onto the additional two phenyl groups from ‐N(Ph) 2 than ‐N(CH 3 ) 2 , that transferred to the whole molecule …”

“…We propose that due to the intermolecular interaction, the molecules become more rigid, and then enhance the fluorescence; the interaction must be strong through the vertices rings. Our results can also explain the aggregation effect on fluorescence …”

Aluminium complexes bearing N,O-aminophenol ligands as efficient catalysts for the ring opening polymerization of lactide

“…The C-H---π contact of 2.81 Å and angle of 149.7° are in correlation with the literature reports and confirm the contribution of CH/π interaction to the molecular network between adjacent molecules [47][48][49][50]. The directionality and the CH/acceptor distance in this interaction are dependent on the strength of CH as a proton donor.…”