Structure Optimization by DFT and Solvatochromism of Series of Dehydroabietic Acid-based Arylamines

Molecular configuration of compounds 5a-5g(methyl 13-(phenyl) aminodeisopropyldehydroabietate( 5a ),Methyl 13-(4-methoxyphenyl) aminodeisopropyldehydroabietate( 5b ),methyl 14-(phenyl) aminodehydroabietate( 5c ),methyl 13-(8-quinoline) aminodeisopropyldehydroabietate( 5d ),methyl 13-(α-naphthalene)aminodeisopropyldehydroabietate( 5e ),methyl 13-(p-bromodiphenyl)aminodeisopropyldehydroabietate( 5f ),methyl 13-(4-methylphenyl)aminodeisopropyldehydroabietate( 5g )) and 6a - 6h (Methyl 13N,N-(4-methoxyphenyl)-phenyl-aminodeisopropyldehydroabietate( 6a ),methyl 13-N,N -(p-bromobiphenyl)-phenylaminodeisopropyldehydroabietate( 6b ),methyl 13-N,N-(4-methylphenyl)-phenylaminodeisopropyldehydroabietate( 6c ),methyl 13-(N,N-bis-phenyl) aminodeisopropyldehydroabietate( 6d ),methyl 13-N,N-bis(4-methoxyphenyl)aminodeisopropyldehydroabietate( 6e ),methyl 13-N,N- (α-naphthalene)-phenylaminodeisopropyldehydroabietate( 6f ),methyl 13-N,N -bis(4-methylphenyl)-phenylaminodeisopropyldehydroabietate( 6g ),methyl 13-N,N-biphenyl-phenylaminodeisopropyldehydroabietate( 6h )) were optimized by DFT/B3LYP using Gaussian 03. Their fluorescent properties in solvents of different polarity were analysed, and the relationship between structures and properties were also discussed. The results show that the conjugated length or substituent groups on aryl rings of compounds have big effect on their conjugated degree, and then affect their fluorescent properties. Compounds 5a-5g , 6f , 6b and 6h have deffrent fluorescent emmision wavelengths and all compounds show defferent fluorescent intensity in defferent polarity solvents. Above properties indicate that these compounds have potential to be used as fluorescent probes in different polarity environment.