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2‐Amino‐3‐naphthylacrylonitrile Derivatives as Green Luminance Dyes
Author(s) -
Lin Richard,
Horng HawChiung,
Lin HsiuMei,
Lin SiYu,
Hon YungSon,
Chow Tashin J.
Publication year - 2010
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201000112
Subject(s) - chemistry , triclinic crystal system , monoclinic crystal system , solvatochromism , crystallography , group (periodic table) , derivative (finance) , ab initio , molecular orbital , crystal structure , stereochemistry , molecule , organic chemistry , financial economics , economics
Three derivatives of 2‐amino‐3‐naphthylacrylonitrile 2∼4 were synthesized as potential green luminance dyes. The green emission is derived from a charge transfer transition, which exhibits an apparent solvatochromic effect. The crystal structures of derivatives 2 and 3 were resolved by X‐ray diffraction analyses. The diphenylamino derivative 2 was found in monoclinic P 21/n space group with a = 10.032(2), b = 17.034(5), c = 12.143(6), and β = 112.02(3)°. The carbazyl derivative 3 was found in triclinic P‐1 space group with a = 8.890(3), b = 9.296(6), c = 12.209(5), and α = 98.89(4)°, β = 93.46(3)°, γ = 116.47(4)°. The amino group in 2 forms a better resonance with acrylonitrile group than that in 3 . The electronic nature of the amino group is responsible for the spectral difference among three compounds. The effect is verified by ab initio molecular modeling.