Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators

碩士 === 國立臺灣師範大學 === 化學系 === 102 === A series of organogelators and metallogelators, DU97, DU135, DU157, DU169 was designed and synthesized. These gelators are composed of ethynylanthrancene and ethynylpyrene derivatives with long-chain pyridine-2,6-dicarboxamide. These gelators have shown great abil...

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Main Author: 呂幸紋
Other Authors: Sun, Shih-Sheng
Format: Others
Language:zh-TW
Published: 2014
Online Access:http://ndltd.ncl.edu.tw/handle/46753197642991193366
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spelling ndltd-TW-102NTNU50650102016-05-22T04:40:27Z http://ndltd.ncl.edu.tw/handle/46753197642991193366 Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators 設計並合成含有醯胺官能基的乙炔蒽和乙炔芘衍生物之有機凝膠分子 呂幸紋 碩士 國立臺灣師範大學 化學系 102 A series of organogelators and metallogelators, DU97, DU135, DU157, DU169 was designed and synthesized. These gelators are composed of ethynylanthrancene and ethynylpyrene derivatives with long-chain pyridine-2,6-dicarboxamide. These gelators have shown great ability to immobilize a variety of organic solvents to form gels. The formation of supramolecular gels is achieved from self-assembly of gelator molecules via cooperative hydrogen bonding, π-π stacking and C-H-π interactions followed by secondary interations with solvent molecules. The presence of aggregates was confirmed by variable-temperature 1H NMR and absorption/emission spectroscopy. The supramolecular aggregates in these organogels are considered to be the J-type aggregation. The xerogels studied by SEM and TEM revealed fiber-like morphologies. Among all gelators, DU97 exhibits the greatest ability to form stable gel in cyclohexane with a critical gelation concentration of 2.9 mg/mL. DU135 and DU157 containing Pt(II) metal centers exhibit unique photophysical properties. DU135 exhibits dual emission with fluorescence at 415 nm and strong phosphorescence at 655 nm. In contrast, DU157 does not show any detectable phosphorescence but only fluorescence at 438 nm. Oxygen addition product was identified for DU157 in chlorinated solvent under UV irradiation. The mechanism for the observed photochemistry likely involves singlet oxygen and proceeds with free-radical pathways. Sun, Shih-Sheng 孫世勝 2014 學位論文 ; thesis 148 zh-TW
collection NDLTD
language zh-TW
format Others
sources NDLTD
description 碩士 === 國立臺灣師範大學 === 化學系 === 102 === A series of organogelators and metallogelators, DU97, DU135, DU157, DU169 was designed and synthesized. These gelators are composed of ethynylanthrancene and ethynylpyrene derivatives with long-chain pyridine-2,6-dicarboxamide. These gelators have shown great ability to immobilize a variety of organic solvents to form gels. The formation of supramolecular gels is achieved from self-assembly of gelator molecules via cooperative hydrogen bonding, π-π stacking and C-H-π interactions followed by secondary interations with solvent molecules. The presence of aggregates was confirmed by variable-temperature 1H NMR and absorption/emission spectroscopy. The supramolecular aggregates in these organogels are considered to be the J-type aggregation. The xerogels studied by SEM and TEM revealed fiber-like morphologies. Among all gelators, DU97 exhibits the greatest ability to form stable gel in cyclohexane with a critical gelation concentration of 2.9 mg/mL. DU135 and DU157 containing Pt(II) metal centers exhibit unique photophysical properties. DU135 exhibits dual emission with fluorescence at 415 nm and strong phosphorescence at 655 nm. In contrast, DU157 does not show any detectable phosphorescence but only fluorescence at 438 nm. Oxygen addition product was identified for DU157 in chlorinated solvent under UV irradiation. The mechanism for the observed photochemistry likely involves singlet oxygen and proceeds with free-radical pathways.
author2 Sun, Shih-Sheng
author_facet Sun, Shih-Sheng
呂幸紋
author 呂幸紋
spellingShingle 呂幸紋
Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators
author_sort 呂幸紋
title Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators
title_short Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators
title_full Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators
title_fullStr Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators
title_full_unstemmed Design and Synthesis of Ethynylanthracene and Ethynylpyrene Derivatives with Amide-functionalized Organogelators
title_sort design and synthesis of ethynylanthracene and ethynylpyrene derivatives with amide-functionalized organogelators
publishDate 2014
url http://ndltd.ncl.edu.tw/handle/46753197642991193366
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