3,5-Bis{3-[4-(dimethylamino)phenyl]prop-2-enylidene}-1-methyl-4-piperidone and 3,5-bis[3-(4-methoxyphenyl)prop-2-enylidene]-1-methyl-4-piperidone: potential biophotonic materials.
The structures of the title compounds, C(28)H(33)N(3)O, (I), and C(26)H(27)NO(3), (II), together with their two-photon absorption properties and fluorescence activities are reported. Molecules of (II) reside on crystallographic mirror planes containing the piperidone C=O group and N-methyl H atoms. Because of the conjugation between the donor and acceptor parts, the central heterocycle in both (I) and (II) exhibits a flattened boat conformation, with deviations of the N atom and the opposite C atom from the planar fragment. The dihedral angles between the coplanar heterocyclic atoms and terminal C(6) rings are less than 20 degrees in both (I) and (II). In (I), the N-methyl group of the ring occupies an equatorial position, but in (II) it is positioned in an axial site. In the crystal structure of (I), weak intermolecular C-H...pi(arene) and C-H...O steric contacts link the molecules along the a axis. In the crystal structure of (II), molecules form stacks along the b axis.
Nesterov
Vladimir N
VN
Department of Natural Sciences, New Mexico Highlands University, Las Vegas, NM 87701, USA. vnesterov@nmhu.edu
Zakharov
Lev N
LN
Sarkisov
Sergey S
SS
Curley
Michael J
MJ
Urbas
Augustine
A
D015502:Absorptiometry, Photon; D018360:Crystallography, X-Ray; D005453:Fluorescence; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D015394:Molecular Structure; D010881:Piperidones / Q000737:chemistry*
C527862:3,5-bis(3-(4-(dimethylamino)phenyl)prop-2-enylidene)-1-methyl-4-piperidone; C527863:3,5-bis(3-(4-methoxyphenyl)prop-2-enylidene)-1-methyl-4-piperidone; D006575:Heterocyclic Compounds, 3-Ring; D010881:Piperidones