Supramolecular Complexation of N-Alkyl- and N,N′-Dialkylpiperazines with Cucurbit[6]uril in Aqueous Solution and in the Solid State

被引：12

作者：

Rekharsky, Mikhail V. ^{[3
,4
]}

Yamamura, Hatsuo ^{[5
]}

Mori, Tadashi ^{[4
]}

Sato, Akihiro ^{[6
]}

Shiro, Motoo ^{[7
]}

Lindeman, Sergey V. ^{[8
]}

Rathore, Rajendra ^{[8
]}

Shiba, Kouhei ^{[9
]}

Ko, Young Ho ^{[1
,2
]}

Selvapalam, Narayanan ^{[1
,2
]}

Kim, Kimoon ^{[1
,2
]}

Inoue, Yoshihisa ^{[3
,4
]}

机构：

[1] Pohang Univ Sci & Technol, Natl Creat Res Initiat Ctr Smart Supramol, Pohang 790784, South Korea

[2] Pohang Univ Sci & Technol, Div Mol & Life Sci, Dept Chem, Pohang 790784, South Korea

[3] JST, ICORP, Entropy Control Project, Suita, Osaka, Japan

[4] Osaka Univ, Dept Appl Chem, Suita, Osaka, Japan

[5] Nagoya Inst Technol, Grad Sch Technol, Showa Ku, Nagoya, Aichi 4668555, Japan

[6] JASCO Int Co, Hachioji, Tokyo 1920046, Japan

[7] Rigaku Corp, Akishima, Tokyo 1968666, Japan

[8] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA

[9] Sysmex Co, Sci Instrumentat Div, Nishi Ku, Kobe, Hyogo 6512271, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 08期

关键词：

crystal design; cucurbiturils; host-guest systems; supramolecular chemistry; thermodynamics; CUCURBITURIL HOMOLOGS; ORGANIC-MOLECULES; HOST; BINDING; CYCLODEXTRIN; DERIVATIVES; INCLUSION; ION; ENCAPSULATION; STABILITY;

D O I：

10.1002/chem.200800398

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Complex stoichiometry/composition and degree of oligomerization (oligomeric supramolecular complex formation) of cucurbit[6]uril (CB[6]) with N-alkyl- and N,N'-dialkylpiperazine were investigated in aqueous solutions by means of isothermal titration calorimetry (ITC), ESI-MS, NMR and light scattering measurements. It was found that the complex stability and the degree of oligomerization increase with elongating the alkyl chain attached to the piperazine core. X-ray crystallographic studies revealed a clear correlation between the structure of CB[6]-alkylpiperazine crystals obtained from aqueous solutions and the molecular weight/properties of host-guest oligomers existed in the solution as supramolecular "seeds" of crystal formation.

引用

页码：1957 / 1965

页数：9

共 50 条

[1] Supramolecular complexation of phenylephrine by cucurbit[7]uril in aqueous solution
Assaf, Khaleel I.
Faraj, Ayah N.
Abu-Nameh, Eyad S. M.
Alnajjar, Mohammad A.
RSC ADVANCES, 2024, 14 (19) : 13286 - 13290
[2] Supramolecular Modification of Ion Chemistry: Modulation of Peptide Charge State and Dissociation Behavior through Complexation with Cucurbit[n]uril (n=5, 6) or α-Cyclodextrin
Zhang, Haizhen
Grabenauer, Megan
Bowers, Michael T.
Dearden, David V.
JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (08): : 1508 - 1517
[3] Supramolecular assemblies controlled by cucurbit[n]uril size (n=6, 7, 8 and 10)
Xu, Weitao
Deng, Xinyu
Xiao, Xin
Bian, Bing
Chen, Qing
Dalgarno, Scott J.
Tao, Zhu
Redshaw, Carl
NEW JOURNAL OF CHEMISTRY, 2020, 44 (11) : 4311 - 4318
[4] Supramolecular assemblies of cucurbit[ n ]urils and 4-aminopyridine controlled by cucurbit[ n ]uril size ( n=5, 6, 7 and 8)
Lu, Yun
Yu, Zhichao
Yang, Xinan
Dai, Jingjing
Shan, Peihui
Feng, Xianhao
Tao, Zhu
Redshaw, Carl
Xiao, Xin
CHINESE CHEMICAL LETTERS, 2023, 34 (07)
[5] Supramolecular assemblies of cucurbit[n]urils and 4-aminopyridine controlled by cucurbit[n]uril size(n = 5, 6, 7 and 8)
Yun Lu
Zhichao Yu
Xinan Yang
Jingjing Dai
Peihui Shan
Xianhao Feng
Zhu Tao
Carl Redshaw
Xin Xiao
Chinese Chemical Letters, 2023, 34 (07) : 157 - 162
[6] Supramolecular assembly of cucurbit[6]uril and N-butyl-4-pyrrolidinopyridine
Hou, Hong-Bo
Gao, Zhong-Zheng
Bai, Dong
Tao, Zhu
Prior, Timothy J.
Redshaw, Carl
Xiao, Xin
SUPRAMOLECULAR CHEMISTRY, 2017, 29 (09) : 680 - 685
[7] Cucurbit[6]uril as ligand for the complexation of lanthanide cations in aqueous solution
Buschmann, HJ
Jansen, K
Schollmeyer, E
INORGANIC CHEMISTRY COMMUNICATIONS, 2003, 6 (05) : 531 - 534
[8] Interaction of Cucurbit[n]uril (n=6-8) with Buflomedil
Yang Xiao-Na
Jiang Song
Li Xin-Jian
Zhu Wei-Guo
Kang Jian-Xun
Zou Da-Peng
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2010, 31 (12): : 2425 - 2430
[9] Cucurbit[n]uril-Based supramolecular separation materials
Zhang, Yu
Zhang, Gengwu
Xiao, Xin
Li, Qing
Tao, Zhu
COORDINATION CHEMISTRY REVIEWS, 2024, 514
[10] Protein recognition by cucurbit[6]uril: high affinity N-terminal complexation
Ramberg, Kiefer O.
Engilberge, Sylvain
Guagnini, Francesca
Crowley, Peter B.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (04) : 837 - 844

← 1 2 3 4 5 →