Donor-pi-acceptor (D-pi-A) polyene dyes are applied as models to study photophysics and are used in photoactive materials. Here we report the synthesis and properties of a dye with a piperidinylphenyl donor (1  ). Starting from commercially available starting materials hexanal and dimethyl malonate, a literature procedure was used to generate and purify 1,5-dibromo-3-pentylpentane (2  ) in five classic synthetic steps. Intramolecular dialkylation of 4-bromoaniline with 2  resulted in 1-(4-bromophenyl)-4-pentylpiperidine (3  ). Lithium-halogen exchange in 3  , followed by reaction with 5-(N,N-diethyl)pentadienal, gave 4-pentyl-(4-piperidinylphenyl)-2,4-pentadienal (4)  . The acceptor was generated through a Knoevenagel condensation of 4  with 1,3-diethyl thiobarbituric acid. The UV and NMR solvatochromic properties in the resulting dye 1  were compared to properties in dyes with related aromatic amine donor groups and a thiobarbituric acid acceptor. 

Synthesis and properties of a donor-pi-acceptor polyene dye with piperidinylphenyl donor

247th National Meeting (2014)

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