Synthesis, crystal structure studies and solvatochromic behaviour of two 2-{5-[4-(dimethylamino)phenyl]penta-2,4-dien-1-ylidene}malononitrile derivatives

The synthesis, crystal structure studies and solvatochromic behavior of 2-{(2E,4E)-5-[4-(dimethylamino)phenyl]penta-2,4-dien-1-ylidene}malononitrile, C16H15N3 (DCV[3]), and 2-{(2E,4E,6E)-7-[4-(dimethylamino)phenyl]hepta-2,4,6-trien-1-ylidene}malononitrile, C18H17N3 (DCV[4]), are reported and discussed in comparison with their homologs having a shorter length of the --conjugated bridge. The compounds of this series have potential use as nonlinear materials with second-order effects due to their donor-acceptor structures. However, DCV[3] and DCV[4] crystallized in the centrosymmetric space group P21/c which excludes their application as nonlinear optical materials in the crystalline state. They both crystallize with two independent molecules having the same molecular conformation in the asymmetric unit. The series DCV[1]-DCV[4] demonstrated reversed solvatochromic behavior in toluene, chloroform, and acetonitrile. © 2019.

Authors
Bogdanov G.1 , Tillotson J.P.2 , Khrustalev V.N. 3 , Rigin S.1 , Timofeeva T.V. 2
Publisher
International Union of Crystallography
Language
English
Pages
1175-1181
Status
Published
Volume
75
Year
2019
Organizations
  • 1 Department of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States
  • 2 School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, United States
  • 3 Research Institute of Chemistry, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation
Keywords
crystal structure.; donoracceptor polyenes; malononitrile; reversed solvatochromism
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