Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives

碩士 === 國立中央大學 === 化學研究所 === 95 === In this study, we demonstrated the reaction between ionic liquid bmimPF6 and acetophenone derivatives. Upon heating constantly, the PF6- anion of bmimPF6 decomposes to fluoride anion and PF5. The strong Lewis acid PF5 then activates acetophenone derivatives easily...

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Main Authors: Po-Neng Chuang, 莊博能
Other Authors: 劉陵崗, 賴重光
Format: Others
Language:zh-TW
Published: 2007
Online Access:http://ndltd.ncl.edu.tw/handle/22756345421353553865
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spelling ndltd-TW-095NCU050650192015-10-13T11:31:57Z http://ndltd.ncl.edu.tw/handle/22756345421353553865 Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives 六氟化磷陰離子協助下甲基苯基酮衍生物之醛醇環三聚合反應研究 Po-Neng Chuang 莊博能 碩士 國立中央大學 化學研究所 95 In this study, we demonstrated the reaction between ionic liquid bmimPF6 and acetophenone derivatives. Upon heating constantly, the PF6- anion of bmimPF6 decomposes to fluoride anion and PF5. The strong Lewis acid PF5 then activates acetophenone derivatives easily to proceed with the aldol condensation to yield dimer(A2-D2), cyclic trimer(A3-D3) and strongly fluorescent pyrilium salt(A4-D4). The more electron-releasing substituent on aryl ring of acetophenone produces more pyrilium salt. The structure of A3-D3, a 1,3,5-triarylbenzene, allows the ring current on the peripheral phenyl rings to affect de-shielding by the inner phenyl ring protons. Hence, the chemical shifts of inner phenyl protons are down-field to those of peripheral phenyl protons. The chemical shifts of protons on 2,4,6-triarylpyrylium core (A4-D4) are further down-field, attributed to the positive charge of pyrylium ring. For the series of A4, B4, and C4, the electron-releasing substituent on peripheral phenyl ring also leads to the down-field shift on the 13C signals of phenyl ring, whereas, with the increase of electron density on the pyrylium ring, the 13C chemical shifts move up-field. Moreover, the stronger electron-releasing substituent on peripheral phenyl ring, the higher red-shift for UV-visible and PL spectra, with also greater quantum yield. 劉陵崗, 賴重光 2007 學位論文 ; thesis 98 zh-TW
collection NDLTD
language zh-TW
format Others
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description 碩士 === 國立中央大學 === 化學研究所 === 95 === In this study, we demonstrated the reaction between ionic liquid bmimPF6 and acetophenone derivatives. Upon heating constantly, the PF6- anion of bmimPF6 decomposes to fluoride anion and PF5. The strong Lewis acid PF5 then activates acetophenone derivatives easily to proceed with the aldol condensation to yield dimer(A2-D2), cyclic trimer(A3-D3) and strongly fluorescent pyrilium salt(A4-D4). The more electron-releasing substituent on aryl ring of acetophenone produces more pyrilium salt. The structure of A3-D3, a 1,3,5-triarylbenzene, allows the ring current on the peripheral phenyl rings to affect de-shielding by the inner phenyl ring protons. Hence, the chemical shifts of inner phenyl protons are down-field to those of peripheral phenyl protons. The chemical shifts of protons on 2,4,6-triarylpyrylium core (A4-D4) are further down-field, attributed to the positive charge of pyrylium ring. For the series of A4, B4, and C4, the electron-releasing substituent on peripheral phenyl ring also leads to the down-field shift on the 13C signals of phenyl ring, whereas, with the increase of electron density on the pyrylium ring, the 13C chemical shifts move up-field. Moreover, the stronger electron-releasing substituent on peripheral phenyl ring, the higher red-shift for UV-visible and PL spectra, with also greater quantum yield.
author2 劉陵崗, 賴重光
author_facet 劉陵崗, 賴重光
Po-Neng Chuang
莊博能
author Po-Neng Chuang
莊博能
spellingShingle Po-Neng Chuang
莊博能
Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives
author_sort Po-Neng Chuang
title Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives
title_short Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives
title_full Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives
title_fullStr Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives
title_full_unstemmed Hexafluorophosphate Anion Assisted Aldol Cyclotrimerization of Acetophenone Derivatives
title_sort hexafluorophosphate anion assisted aldol cyclotrimerization of acetophenone derivatives
publishDate 2007
url http://ndltd.ncl.edu.tw/handle/22756345421353553865
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