| Summary: | 碩士 === 國立中央大學 === 化學研究所 === 89 === This thesis consists of two independent sections. The first section is the studies on the synthesis and photochemical behavior of trans-3-aminostilbene and its N-phenyl substituted derivatives. Several 3-amino and 4-N,N-diphenylamino substituted 1,2-diarylethylenes are also included. Target compounds were prepared based on the Horner-Emmons olefin synthesis, Pd-catalyzed C-N coupling reaction, and N-methylation reaction. Absorption spectra show blue shifts with increased intensity for 3-aminostilbenes upon N-phenyl substitutions; however, it is red-shifted in fluorescence spectra. Fluorescence quantum yields decrease for N-phenyl substituted 3-aminostilbenes, but the decrease in fluorescence quantum yields is only little for the case of N-phenyl group that contains dimethyl substituents at the 2 and 6 positions. These observations indicate that the fluorescence behavior of N-phenyl substituted 3-aminostilbenes is strongly related to the extent of conjugation between the amine and stilbene groups and is opposite to that of N-phenyl substituted 4-aminostilbenes.
The second section is the synthesis of a new pentiptycene-derived dithiol for the investigation of its self-assembly behavior on the metal surface. This project follows the previous work in this laboratory and aims to improve the ordering of self-assembled monolayer by introducing the potential hydrogen-bonding amide groups to the alkyl chains. The synthetic procedures involve six steps, including SN2 reaction, deprotecting reaction, and DCC coupling reaction.
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