Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes
作者:
Meng Gao;Yan Yang;Yan-Dong Wu;Cong Deng;Li-Ping Cao;...
期刊:
Organic Letters ,2010年12(8):1856-1859 ISSN:1523-7060
通讯作者:
Wu, An-Xin
作者机构:
[An-Xin Wu; Li-Ping Cao; Meng Gao; Yan Yang; Yan-Dong Wu; Xiang-Gao Meng; Cong Deng] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones.
语种:
英文
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New fluorescent probes based on supramolecular diastereomers for the detection of 2-nitrophenol
作者:
Li, Lin;Sun, Yichong;Wang, Shuai;Qiu, Mingqiang;Wu, Anxin
* ( 吴安心 )
期刊:
Talanta ,2010年81(4-5):1643-1649 ISSN:0039-9140
通讯作者:
Wu, Anxin
作者机构:
[Wu, Anxin; Li, Lin; Sun, Yichong; Qiu, Mingqiang] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Sun, Yichong] ZhongShan 1 Middle Sch, Zhongshan 528403, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词:
Fluorescent probes;2-nitrophenol;Diethoxycarbonyl glycoluril;Supramolecular diastereomers
摘要:
A couple of new fluorescent probes, based on diethoxycarbonyl glycoluril, were synthesized and characterized by <sup>1</sup>H NMR, X-ray crystal structure. The probes were found to be relatively highly fluorescence with quantum yields of 0.20 and 0.18, respectively, at room temperature in THF solution. Both of the proposed probes were tested using different phenolic compounds, showing very high selectivity and sensitivity for 2-nitrophenol by forming a 1:1 complex in THF-MeOH (9:1, v/v). Additionally, the sensors could be used for the qualitative analysis of 2-nitrophenol in real water samples. ©2010 Elsevier B.V. All rights reserved.
语种:
英文
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Thioglycoluril as a Novel Organocatalyst: Rapid and Efficient alpha-Monobromination of 1,3-Dicarbonyl Compounds
作者:
Cao, Liping;Ding, Jiaoyang;Yin, Guodong;Gao, Meng;Li, Yitao;...
期刊:
SYNLETT ,2009年2009(9):1445-1448 ISSN:0936-5214
作者机构:
[Wu, Anxin; Yin, Guodong; Li, Yitao; Cao, Liping; Gao, Meng; Ding, Jiaoyang] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词:
organocatalysis;thioglycoluril;hydrogen bond;alpha-monobromination;1,3-dicarbonyl compounds
摘要:
Thioglycoluril as a novel hydrogen-bonding organocatalyst, combined with NBS, in MeOH provided rapid and efficient α-monobromination of 1,3-dicarbonyl compounds in excellent yields at room temperature. A bifunctional catalytic mechanism was proposed from these results. © Georg Thieme Verlag Stuttgart.
语种:
英文
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Synthesis and Recognition Properties of Two Novel Concave Molecules Based on Glycoluril
作者:
Wang Shuai
( 佘能芳 ) ;Wu An-Xin
( 吴安心 ) ;She Neng-Fang
*
期刊:
Journal of Chemical Research ,2009年2009(4):265-268 ISSN:1747-5198
作者机构:
[Wang Shuai; Wu An-Xin; She Neng-Fang] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[She Neng-Fang] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
glycoluril molecular clip;recognition;Fe(III)
摘要:
Two new concave fluorescent molecular clips based on diethoxycarbonyl glycoluril and diphenyl acetylene units have been synthesised by introducing the fluorophores into the receptor. Their recognition properties toward various metal ions were studied by fluorescence spectroscopy. The results demonstrate that they can selectively bind Fe3+ with fluorescence quenching.
语种:
英文
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A concise and efficient way to synthesize polyenic diones directly from α,β-unsaturated methyl ketones
作者:
Gao, Meng;Yin, Guodong;Wang, Zihua;Wu, Yandong;Guo, Cheng;...
期刊:
Tetrahedron ,2009年65(31):6047-6049 ISSN:0040-4020
作者机构:
[Wu, Anxin; Yin, Guodong; Gao, Meng; Wu, Yandong; Wang, Zihua] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Guo, Cheng; Pan, Yuanjiang] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词:
Polyenic diones;Self-sorting tandem;alpha,beta-Unsaturated methyl ketones;Dimethyl sulfoxide
摘要:
A concise and efficient approach to polyenic compounds containing important diketone structural fragments is developed from readily available α,β-unsaturated methyl ketones in the presence of copper(II) oxide, iodine, and dimethyl sulfoxide. This is a new carbon–carbon double bond-forming reaction from two methyl sp3 C–H bonds and an attractive route to introduce the SMe group into the molecule from inexpensive dimethyl sulfoxide. The hypothetic self-sorting tandem reaction mechanism is also proposed in this paper.
语种:
英文
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Synthesis of Self-Folded Molecular Rotors Controlled by Edge-to-Face CH/pi Aromatic Interactions
作者:
Li, Yitao;Zhu, Yanping;Qin, Jing;Guo, Huizhen;Li, Lin;...
期刊:
SYNLETT ,2009年2009(12):2028-2034 ISSN:0936-5214
作者机构:
[Wu, Anxin; Li, Yitao; Li, Lin; Zhu, Yanping; Qin, Jing; Guo, Huizhen] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词:
self-folded;molecular rotors;CH/p interactions;molecular clips;diethoxycarbonyl glycoluril
摘要:
A series of novel self-folded molecular rotors were synthesized and characterized by 1H NMR, 13C NMR, HRMS, and IR data. All but two compounds were also studied by X-ray crystallography. © Georg Thieme Verlag Stuttgart.
语种:
英文
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Synthesis of Novel Molecular Clips via Click Chemistry Based on Diethoxy carbonyl Glycoluril
作者:
Gao, Meng;Cao, Liping;Wang, Zihua;Sun, Jingjing;She, Nengfang
( 佘能芳 ) ;...
期刊:
SYNLETT ,2009年2009(2):315-319 ISSN:0936-5214
作者机构:
[She, Nengfang; Wu, Anxin; Sun, Jingjing; Cao, Liping; Gao, Meng; Wang, Zihua] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
clip receptor;diethoxycarbonyl glycoluril;molecular recognition;1,2,3-triazole;fluorescence
摘要:
A novel class of molecular clips based on diethoxycarbonyl glycoluril was synthesized via click chemistry. Seven different arylacetylenes were used in this research, and all reaction products gave satisfying 1H NMR, 13C NMR, HRMS, and IR spectra. The structure and conformation of 7a were further confirmed by single-crystal X-ray diffraction. A primary study on the metal-ion binding ability of 7f showed that its fluorescence was obviously quenched by Fe3+, Ag+, and Cu2+ among metal ions examined. © Georg Thieme Verlag Stuttgart.
语种:
英文
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Synthesis and binding properties of two new fluorescent molecular clips based on diethoxycarbonyl glycoluril:
作者:
Hu Sheng-Li;Wang Shuai;Li Yi-Tao;Cao Li-Ping;Wu An-Xin
* ( 吴安心 )
期刊:
Journal of Chemical Research ,2009年2009(1):32-34 ISSN:1747-5198
作者机构:
[Wu An-Xin; Hu Sheng-Li; Cao Li-Ping; Li Yi-Tao; Wang Shuai] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Hu Sheng-Li] Hubei Normal Univ, Dept Chem & Enviromental Engn, Huangshi 435002, Peoples R China.
通讯机构:
[Wu An-Xin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
diethoxycarbonyl glycoluril;molecular clip;fluorescence quenching;Fe3+
摘要:
Two new fluorescent molecular clips based on diethoxycarbonylglycoluril have been synthesised and their binding properties investigated by fluorescence spectroscopy to show that they can selectively bind Fe3+ with fluorescence quenching.
语种:
英文
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Supramolecular rhombic grids formed from bimolecular building blocks
作者:
She, Neng-Fang
( 佘能芳 ) ;Gao, Meng;Meng, Xiang-Gao;Yang, Guang-Fu
( 杨光富 ) ;Elemans, Johannes A A W;...
期刊:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY ,2009年131(33):11695-11697 ISSN:0002-7863
作者机构:
[She, Neng-Fang; Yang, Guang-Fu; Wu, An-Xin; Gao, Meng; Meng, Xiang-Gao] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Elemans, Johannes A A W] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands.;[Isaacs, Lyle] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
(Figure Presented) A programmed assembly process produces rhombic grid networks from compounds L1-L4 in the crystal by π-π stacking interactions that generate a bimolecular grid synthon, which undergoes further NH⋯N hydrogen-bond-mediated assembly. © 2009 American Chemical Society.
语种:
英文
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Solvent Effect on pseudopolymorphisni of hemicyclohexylcucurbit[6]uril
作者:
Li, Yitao;Li, Lin;Zhu, Yanping;Meng, Xianggao;Wu, Anxin
* ( 吴安心 )
期刊:
Crystal Growth & Design ,2009年9(10):4255-4257 ISSN:1528-7483
作者机构:
[Wu, Anxin; Li, Yitao; Li, Lin; Zhu, Yanping; Meng, Xianggao] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
Novel covalent macrocycle, hmcyCuco6, has been synthesized and its four pseudopolymorphs were reported. HmcyCuco6 is highly selective to CH 2Cl2, CHCl3, and CCl4 in the crystal growth, and the selectivity of the hmcyCucó toward these solvent molecules may be related to the symmetry of the solvent molecules. In addition, four pseudopolymorphs can be simply controlled by changing the crystallization, solvent system. To our best knowledge, the pseudopolymorphism. of the cucurbit[w]uril homologues is reported for the first time. © 2009 American Chemical Society.
语种:
英文
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Synthesis of novel unsymmetrical molecular clips derived from glycoluril:
作者:
Hu Sheng-Li;Wu Yan-Dong;Cao Li-Ping;Wu An-Xin
* ( 吴安心 )
期刊:
Journal of Chemical Research ,2009年2009(7):414-415 ISSN:1747-5198
作者机构:
[Wu An-Xin; Wu Yan-Dong; Hu Sheng-Li; Cao Li-Ping] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Hu Sheng-Li] Hubei Normal Univ, Dept Chem & Environm Engn, Huangshi 435002, Peoples R China.
通讯机构:
[Wu An-Xin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
glycoluril;unsymmetrical;molecular clip
摘要:
Four novel unsymmetrical molecular clips derived from glycoluril have been designed and synthesised and the structure and conformation of one was also confirmed by single crystal X-ray diffraction.
语种:
英文
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Sensor for Nitrophenol Based on a Fluorescent Molecular Clip
作者:
She, Nengfang
( 佘能芳 ) ;Gao, Meng;Cao, Liping;Wu, Anxin
* ( 吴安心 ) ;Isaacs, Lyle
期刊:
Organic Letters ,2009年11(12):2603-2606 ISSN:1523-7060
作者机构:
[She, Nengfang; Wu, Anxin; Cao, Liping; Gao, Meng] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Isaacs, Lyle] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA.;[Wu, Anxin] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Peoples R China.
摘要:
We report the synthesis, X-ray crystal structure, and photophysics of a fluorescent molecular clip (1). Binding studies of 1 toward phenols 2a-j were carried out using fluorescence, (1)H NMR, and IR spectroscopy, which revealed a high affinity and selectivity for 4-nitrophenol (2a) due to formation of the 1.2a complex driven by H-bonding and pi-pi stacking interactions.
语种:
英文
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Synthesis, crystal structure, binding properies of a noncyclic crown-type receptor derived from diethoxycarbonyl glycoluril:
作者:
Zhou Bao-Han
* ;Cao Li-Ping;Wu An-Xin
( 吴安心 )
期刊:
Journal of Chemical Research ,2009年2009(7):440-442 ISSN:1747-5198
通讯作者:
Zhou Bao-Han
作者机构:
[Zhou Bao-Han] Hu Bei Univ Technol, Chem & Environm Engn Dept, Wuhan 430068, Peoples R China.;[Wu An-Xin; Cao Li-Ping] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Zhou Bao-Han] H;Hu Bei Univ Technol, Chem & Environm Engn Dept, Wuhan 430068, Peoples R China.
关键词:
noncyclic crown-type;crystal structure;binding properies
摘要:
A novel noncyclic crown-type diethoxycarbonyl glycoluril derivative receptor was synthesised and its crystal structure was obtained. The study of its binding behaviour towards neutral guests showed that it can bind hydroquinone, resorcinol and catechol.
语种:
英文
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Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia
作者:
Cao, Liping;Ding, Jiaoyang;Gao, Meng;Wang, Zihua;Li, Juan;...
期刊:
Organic Letters ,2009年11(17):3810-3813 ISSN:1523-7060
作者机构:
[Wu, Anxin; Cao, Liping; Gao, Meng; Li, Juan; Ding, Jiaoyang; Wang, Zihua] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Wu, Anxin] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
Figur Presented A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH 3 ·H 2 O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time. © 2009 American Chemical Society.
语种:
英文
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Synthesis and X-ray Structure of New Molecular Clips Based on diphenylglycoluril:
作者:
Hu Sheng-Li;Wu Yan-Dong;Li Jing;Wang Kun-Ru;Wu An-Xin
* ( 吴安心 )
期刊:
Journal of Chemical Research ,2009年2009(7):418-419 ISSN:1747-5198
作者机构:
[Wu An-Xin; Wu Yan-Dong; Hu Sheng-Li; Li Jing; Wang Kun-Ru] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Hu Sheng-Li] Hubei Normal Univ, Dept Chem & Enviromental Engn, Huangshi 435002, Peoples R China.
通讯机构:
[Wu An-Xin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
diphenyl glycoluril;molecular clip;1, 2-dihydro-indazol-3-one
摘要:
A pair of new molecular clips based on diphenylglycoluril and 1, 2-dihydroindazol-3-one have been synthesised. Their structures and conformations were confirmed by single crystal X-ray diffraction.
语种:
英文
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Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions
作者:
Yin, Guodong;Gao, Meng;Wang, Zihua;Wu, Yandong;Wu, Anxin
* ( 吴安心 )
期刊:
Bulletin of the Chemical Society of Japan ,2008年81(3):369-372 ISSN:0009-2673
通讯作者:
Wu, Anxin
作者机构:
[Wu, Anxin; Yin, Guodong; Gao, Meng; Wang, Zihua] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Wu, Yandong] Xiangtan Univ, Coll Chem, Xiangtan 411105, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
Aromatic methyl ketones, ß-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods. © 2008 The Chemical Society of Japan.
语种:
英文
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An Efficient Method for the Selective Iodination of alpha,beta-Unsaturated Ketones
作者:
Wang, Zihua;Yin, Guodong;Qin, Jing;Gao, Meng;Cao, Liping;...
期刊:
SYNTHESIS-STUTTGART ,2008年2008(22):3675-3681 ISSN:0039-7881
作者机构:
[Wu, Anxin; Yin, Guodong; Cao, Liping; Gao, Meng; Qin, Jing; Wang, Zihua] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词:
iodination;alpha,beta-unsaturated ketones;alpha,beta-unsaturated alpha '-iodo ketones;self-sorting
摘要:
An efficient approach to alpha,beta-unsaturated alpha'-iodo ketones directly from alpha,beta-unsaturated ketones by selective iodination at the alpha'-position, without effect on the double bond and the activated benzene ring, in the presence of copper(II) oxide/iodine is described. The present method has the advantages of high yields, short reaction times, inexpensive reagents, mild reaction conditions, ease of manipulation, and the formation of cleaner products.
语种:
英文
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竞争性氢键调控的二聚组装
作者:
高蒙;曹利平;郭成;孙静静;黄飞虎;...
作者机构:
[佘能芳; 吴安心; 高蒙; 曹利平; 郭成; 孙静静; 黄飞虎] 华中师范大学化学学院农药与化学生物学教育部重点实验室
会议名称:
全国第十四届大环化学暨第六届超分子化学学术讨论会
会议时间:
2008-08
会议地点:
中国甘肃兰州
关键词:
二乙酯基甘脲;分子夹;竞争性氢键
摘要:
制备并得到了三种基于二乙酯基甘脲的手性分子夹的晶体结构。在竞争性氢键的作用下,该类分子夹形成了含有更强氢键给体的边墙相扣的中心对称的二聚结构。
语种:
中文
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Synthesis, X-ray structure, and binding properties of a new fluorescent molecular clip derived from diethoxycarbonyl glycoluril
作者:
Hu, Sheng-Li
* ;Yin, Guo-Dong;Wang, Yu-Zhou;Wu, An-Xin
( 吴安心 )
期刊:
CANADIAN JOURNAL OF CHEMISTRY ,2008年86(7):691-694 ISSN:0008-4042
作者机构:
[Wu, An-Xin; Hu, Sheng-Li; Wang, Yu-Zhou; Yin, Guo-Dong] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Hu, Sheng-Li] Hubei Normal Univ, Hubei Key Lab Bioanalyt Tech, Huangshi 435002, Peoples R China.
通讯机构:
[Hu, Sheng-Li] H;Hubei Normal Univ, Hubei Key Lab Bioanalyt Tech, Huangshi 435002, Peoples R China.
关键词:
Diethoxycarbonyl glycoluril;Fe(III);Fluorescence;Molecular clip
摘要:
A new fluorescent molecule clip derived from diethoxycarbonyl glycoluril with two 2,5-diphenyl-furan side-walls was designed and synthesized. Its structure and conformation was confirmed by single-crystal X-ray diffraction. Its binding properties, investigated by fluorescence spectroscopey, showed that it can selectively bind Fe3+ with fluorescence quenching. © 2008 NRC Canada.
语种:
英文
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Self-sorting molecular clips
作者:
Ghosh, Soumyadip;Wu, Anxin
* ( 吴安心 ) ;Fettinger, James C.;Zavalij, Peter Y.;Isaacs, Lyle
期刊:
JOURNAL OF ORGANIC CHEMISTRY ,2008年73(15):5915-5925 ISSN:0022-3263
作者机构:
[Ghosh, Soumyadip; Fettinger, James C.; Isaacs, Lyle; Zavalij, Peter Y.] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA.;[Wu, Anxin] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
(Figure Presented) We report the synthesis and characterization of 12 C-shaped methylene-bridged glycoluril dimers (1-12) bearing H-bonding groups on their aromatic rings. Compounds 1, 2, (±)-4a, (±)-5, (±)-7, and 8 form tightly associated homodimers in CDCl<inf>3</inf>, due to the combined driving force of π,πand H-bonding interactions. Compounds 2, (±)-5, and 8, having disparate spatial distribution of their H-bonding groups, display the ability to efficiently distinguish between self and nonself even within three-component mixtures in CDCl<inf>3</inf>. When the spatial distributions of the H-bonding groups of the molecular clips are similar (e.g., 1 and 2), a mixture of homodimers and heterodimers is formed. The effect of various structural modifications (e.g., chirality, side chain steric bulk, number and pattern of H-bonds) on the strength of self-assembly and the fidelity of self-sorting are presented. On the basis of these results we prepared self-sorting systems comprising three (e.g., 1, (±)-5, and (±)-7) and even four (2, (±)-5, 9, and 10) components. The potential of molecular clips 1-12 as robust, functionalizable, self-sorting modules to control the noncovalent interaction network in systems chemistry studies is described. ©2008 American Chemical Society.
语种:
英文
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