Studies On The Synthesis And Spectral Properties Of 1,8-naphthalene Imide Derivatives

1,8-Naphthalene imide derivatives were an attractive class of organic dyes with excellent photo-and thermal stability.Through chemical modifications,their optical,electronic as well as chemical properties can be improved and thus find the potential applications in photovoltaic cells,sensors,ion transports and organic catalysis,et al.Thus,in this thesis,three 4-hydroxyphenyl-substituted 1,8-naphthalene imides,i.e.,NMI2a,NMI2b,NMI2c,have been succusfully synthesized from commercially available 1,8-naphthalenedicarboxylic acid anhydride in three steps.The conspecific interconnection of them by three different spacers,such as 1,4-benzyl bromide,1,2-benzyl bromide and 1,4-dibromobutane leads to nine bisnaphthalene diimide dyes 1-9.All the intermediates and final products have been fully characterized by NMR as well as mass spectroscopy.In addition,the structure of compound 1 has also been confirmed by X-ray single crystal diffraction analysis.The absorption,fluorescence,solvatochromism as well as solubilities of all the obtained 1,8-naphthalene imides and bisnaphthalene diimides have been investigated by UV-Vis-NIR and fluorescent spectroscopies,and several useful results can be obtained as following:(1)The deprotonation of NMI2a,NMI2b and NMI2c by tetrabutylammonium hydroxide leads to respective phenolate derivatives with a positive solvatochromism.(2)The solubility of nice bisnaphthalene diimides is mainly dependent on their spacers in an order of 1,2-benzyl>1,4-butyl>1,4-benzyl,which is attributed to the configuration of the spacer unit.(3)At the same time,the solubility is also controlled by the substituents at the imide positions with an order of 2,6-diisopropylphenyl>hexyl?cyclohexyl,which is attributed to the steric hindrances.(4)Upon addition of aniline,the fluorescence of all nine bisnaphthalene diimides can be quenched,which may find an application for detection of those containing amines.