摘要
Two new diarylamine-substituted 1, 8-naphthalimide derivatives are synthesized by Cu I/18-crown-6/K2CO3 catalyst system and characterized by Fourier transform infrared （FT- IR）, ^1H-NMR and elemental analyses. The UV-vis absorption and photoluminescent （PL）spectra of the systems in n-hexane, tetrahydrofuran（THF）, and CH2Cl2 are investigated. These naphthalimide molecules have an absorption band centered at about 450 nm, which is assigned to an intramolecular chargetransfer （ICT）transition, and they emit light at 492, 501 nm in a nonpolar solvent such as n-hexane, and at 600, 620 nm in a polar solvent such as CH2Cl2. From the Lippert-Mataga equation, the difference of the dipole moment between the excited state and the ground state is estimated to be 9.2 and 9.8 D for 4- （ diphenylamine ）-N-（ 2-methoxyphenyl ）-1, 8-naphthalimide （ DMN-1 ） and 4-（ 2-naphthylphenylamine ）-N-（ 2- methoxyphenyl）-1, 8-naphthalimide （DMN-2）, respectively. This large change in the dipole moment upon excitation is typical for photoinduced ICT processes.
以二芳胺和4-溴-1,8-萘酰亚胺体系为原料,经CuⅠ/18-crown-6/K2CO3催化制备了2个新的萘酰亚胺衍生物,利用FT-IR,NMR,EA等表征了其结构.并用UV-vis和PL测定了此类化合物在正己烷、四氢呋喃和二氯甲烷不同极性溶剂中的发光性能.在450nm附近的紫外最大吸收波长是由于分子内的电荷转移造成的,并且其发射波长在非极性溶剂正己烷中分别位于492和501nm,而在极性溶剂二氯甲烷中分别位于600和620nm.采用Lippert-Mataga方程计算出分子4-二苯胺基-N-(2-甲氧基苯基)-1,8-萘酰亚胺(DMN-1)和4-(2-萘基苯基胺基)-N-(2-甲氧基苯基)-1,8-萘酰亚胺(DMN-2)基态与激发态偶极矩差值分别为9.2和9.8D,如此大的偶极矩变化说明了该分子具有典型的分子内电荷转移特性.
基金
The Ph.D.Programs Foundation of Ministry of Educa-tion of China(No.20030286012)
the High Technology Research and De-velopment Program of Jiangsu Province(No.BG2005034)
