Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes
碩士 === 國立中央大學 === 化學研究所 === 90 === This thesis is a follow-up study on the “amino conjugation effect” of trans-4-aminostilbenes. N-phenyl substitution of trans-4-aminostilbene leads to a more planar ground-state geometry about the amino nitrogen atom, a larger charge-transfer character, a slower ra...
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ndltd-TW-090NCU050650152015-10-13T10:10:53Z http://ndltd.ncl.edu.tw/handle/53910101240426509743 Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes 取代基效應對反式-4-(N-苯基)二苯乙烯胺之光化學行為影響之研究 Kang-ling Liau 廖康廩 碩士 國立中央大學 化學研究所 90 This thesis is a follow-up study on the “amino conjugation effect” of trans-4-aminostilbenes. N-phenyl substitution of trans-4-aminostilbene leads to a more planar ground-state geometry about the amino nitrogen atom, a larger charge-transfer character, a slower rate constant for photoisomerization, and thus a higher fluorescence quantum yield. To investigate the substituent effect on the photochemical behavior of trans-4-N-phenylaminostilbene, we have synthesized compound series 2-6, which have substituents on the N-phenylamino group, and compound series 7 and 8, which contain strong electron-withdrawing groups at the 4’ position of the stilbene group. More detained photochemical studies were performed on compound series 2 and 7. Electron-donating groups result in red-shifted absorption and emission spectra for compounds 2, which is valid in a variety of solvents. In hexane, the fluorescence quantum yield of compound 2 is larger for substituents with a stronger electron-withdrawing ability. Such a behavior is however not observed in other solvents. When the substituent in 2 is an ester or a cyano group, the fluorescence quantum yield is particular low in medium or polar solvents, which can be attributed to the formation of twisted internal charge-transfer (TICT) states. In the case of compounds 7, a significant solvent-dependent fluorescence spectra were recorded as a result of the presence of both strong electron-donating and electron-withdrawing groups. In polar solvents, both fluorescence and photoisomerization quantum yields are low, which might be a consequence of TICT formation. Jye-Shane Yang 楊吉水 2002 學位論文 ; thesis 194 zh-TW |
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碩士 === 國立中央大學 === 化學研究所 === 90 ===
This thesis is a follow-up study on the “amino conjugation effect” of trans-4-aminostilbenes. N-phenyl substitution of trans-4-aminostilbene leads to a more planar ground-state geometry about the amino nitrogen atom, a larger charge-transfer character, a slower rate constant for photoisomerization, and thus a higher fluorescence quantum yield.
To investigate the substituent effect on the photochemical behavior of trans-4-N-phenylaminostilbene, we have synthesized compound series 2-6, which have substituents on the N-phenylamino group, and compound series 7 and 8, which contain strong electron-withdrawing groups at the 4’ position of the stilbene group. More detained photochemical studies were performed on compound series 2 and 7.
Electron-donating groups result in red-shifted absorption and emission spectra for compounds 2, which is valid in a variety of solvents. In hexane, the fluorescence quantum yield of compound 2 is larger for substituents with a stronger electron-withdrawing ability. Such a behavior is however not observed in other solvents. When the substituent in 2 is an ester or a cyano group, the fluorescence quantum yield is particular low in medium or polar solvents, which can be attributed to the formation of twisted internal charge-transfer (TICT) states.
In the case of compounds 7, a significant solvent-dependent fluorescence spectra were recorded as a result of the presence of both strong electron-donating and electron-withdrawing groups. In polar solvents, both fluorescence and photoisomerization quantum yields are low, which might be a consequence of TICT formation.
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author2 |
Jye-Shane Yang |
author_facet |
Jye-Shane Yang Kang-ling Liau 廖康廩 |
author |
Kang-ling Liau 廖康廩 |
spellingShingle |
Kang-ling Liau 廖康廩 Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes |
author_sort |
Kang-ling Liau |
title |
Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes |
title_short |
Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes |
title_full |
Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes |
title_fullStr |
Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes |
title_full_unstemmed |
Studies on the Substituent Effects on the Photochemical Behavior of trans-4-(N-Phenylamino)stilbenes |
title_sort |
studies on the substituent effects on the photochemical behavior of trans-4-(n-phenylamino)stilbenes |
publishDate |
2002 |
url |
http://ndltd.ncl.edu.tw/handle/53910101240426509743 |
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