Complexation of Ferrocene Derivatives by the Cucurbit[7]uril
Host: A Comparative Study of the Cucurbituril and Cyclodextrin
Host Families

J 2005

Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families

JEON, Woo Sung, Kwangyul MOON, Sang Hyun PARK, Hyungpil CHUN, Young Ho KO et. al.

Basic information

Original name

Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families

Name in Czech

Komplexace derivátu ferrocenu a cucurbit[7]urilu: Porovnávací studie skupiny cucurbiturilů and cyclodextrinů

Authors

JEON, Woo Sung (410 Republic of Korea), Kwangyul MOON (410 Republic of Korea), Sang Hyun PARK (410 Republic of Korea), Hyungpil CHUN (410 Republic of Korea), Young Ho KO (410 Republic of Korea), Jin Yong LEE (410 Republic of Korea), Eun Sung LEE (410 Republic of Korea), S. SAMAL (410 Republic of Korea), N. SELVAPALAM (410 Republic of Korea), Mikhail V REKHARSKY (392 Japan), Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor), David SOBRANSINGH (410 Republic of Korea), Yoshihisa INOUE (392 Japan), Angel E KAIFER (840 United States of America) and Kimoon KIM (410 Republic of Korea)

Edition

Journal of the American Chemical Society, Washington, D.C. American Chemical Society, 2005, 0002-7863

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10404 Polymer science

Country of publisher

Czech Republic

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 7.419

RIV identification code

RIV/00216224:14310/05:00031282

Organization unit

Faculty of Science

UT WoS

000231928800055

Keywords in English

cucurbiturils; self-assembly

Abstract

ORIG CZ

V originále

The formation of inclusion complexes between cucurbit[7]uril (CB[7]) and ferrocene and its derivs. has been investigated. The x-ray crystal structure of the 1:1 inclusion complex between ferrocene and CB[7] revealed that the guest mol. resides in the host cavity with two different orientations. Inclusion of a set of five water-sol. ferrocene derivs. in CB[7] was investigated by 1H NMR spectroscopy and calorimetric and voltammetric techniques. Data indicate that all neutral and cationic guests form highly stable inclusion complexes with CB[7], with binding consts. in the 109-1010 M-1 and 1012-1013 M-1 ranges, resp. However, the anionic ferrocenecarboxylate, the only neg. charged guest among those surveyed, was not bound by CB[7] at all. These results are in sharp contrast to the known binding behavior of the same guests to b-cyclodextrin (b-CD), since all the guests form stable inclusion complexes with b-CD, with binding consts. in the range 103-104 M-1. The electrostatic surface potentials of CB[6], CB[7], and CB[8] and their size-equiv. CDs were calcd. and compared. The CD portals and cavities exhibit low surface potential values, whereas the regions around the carbonyl oxygens in CBs are significantly neg., which explains the strong affinity of CBs for pos. charged guests and also provides a rationalization for the rejection of anionic guests. Taken together, our data suggest that cucurbiturils may form very stable complexes. However, the host-guest interactions are very sensitive to some structural features, such as a neg. charged carboxylate group attached to the ferrocene residue, which may completely disrupt the stability of the complexes.

In Czech

Je popsán vznik inkluzivních komplexů mezi cucurbit[7]urilem (CB[7]) and ferrocene a jeho deriváty. Krystalová struktura 1:1 komplexu mezi CB[7] a ferrocenem ukázala, že hostitelská molekula se nachází uvnitř kavity hosta ve dvou rozdílných orientacích. Ke stanocení konstant stability těchto komplexů a způsobu interakce byly použity NMR, cyklická voltametrie a kalorimetrie.

Citovat

JEON, Woo Sung, Kwangyul MOON, Sang Hyun PARK, Hyungpil CHUN, Young Ho KO, Jin Yong LEE, Eun Sung LEE, S. SAMAL, N. SELVAPALAM, Mikhail V REKHARSKY, Vladimír ŠINDELÁŘ, David SOBRANSINGH, Yoshihisa INOUE, Angel E KAIFER and Kimoon KIM. Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families. Journal of the American Chemical Society. Washington, D.C.: American Chemical Society, 2005, vol. 127, No 37, p. 12984-12989. ISSN 0002-7863.

@article{601365,
   author = {Jeon, Woo Sung and Moon, Kwangyul and Park, Sang Hyun and Chun, Hyungpil and Ko, Young Ho and Lee, Jin Yong and Lee, Eun Sung and Samal, S. and Selvapalam, N. and Rekharsky, Mikhail V and Šindelář, Vladimír and Sobransingh, David and Inoue, Yoshihisa and Kaifer, Angel E and Kim, Kimoon},
   article_location = {Washington, D.C.},
   article_number = {37},
   keywords = {cucurbiturils; self-assembly},
   language = {eng},
   issn = {0002-7863},
   journal = {Journal of the American Chemical Society},
   title = {Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families},
   volume = {127},
   year = {2005}
}

TY  - JOUR
ID  - 601365
AU  - Jeon, Woo Sung - Moon, Kwangyul - Park, Sang Hyun - Chun, Hyungpil - Ko, Young Ho - Lee, Jin Yong - Lee, Eun Sung - Samal, S. - Selvapalam, N. - Rekharsky, Mikhail V - Šindelář, Vladimír - Sobransingh, David - Inoue, Yoshihisa - Kaifer, Angel E - Kim, Kimoon
PY  - 2005
TI  - Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families
JF  - Journal of the American Chemical Society
VL  - 127
IS  - 37
SP  - 12984-12989
EP  - 12984-12989
PB  - American Chemical Society
SN  - 00027863
KW  - cucurbiturils
KW  - self-assembly
N2  - The formation of inclusion complexes between cucurbit[7]uril (CB[7]) and ferrocene and its derivs. has been investigated. The x-ray crystal structure of the 1:1 inclusion complex between ferrocene and CB[7] revealed that the guest mol. resides in the host cavity with two different orientations. Inclusion of a set of five water-sol. ferrocene derivs. in CB[7] was investigated by 1H NMR spectroscopy and calorimetric and voltammetric techniques. Data indicate that all neutral and cationic guests form highly stable inclusion complexes with CB[7], with binding consts. in the 109-1010 M-1 and 1012-1013 M-1 ranges, resp. However, the anionic ferrocenecarboxylate, the only neg. charged guest among those surveyed, was not bound by CB[7] at all. These results are in sharp contrast to the known binding behavior of the same guests to b-cyclodextrin (b-CD), since all the guests form stable inclusion complexes with b-CD, with binding consts. in the range 103-104 M-1. The electrostatic surface potentials of CB[6], CB[7], and CB[8] and their size-equiv. CDs were calcd. and compared. The CD portals and cavities exhibit low surface potential values, whereas the regions around the carbonyl oxygens in CBs are significantly neg., which explains the strong affinity of CBs for pos. charged guests and also provides a rationalization for the rejection of anionic guests. Taken together, our data suggest that cucurbiturils may form very stable complexes. However, the host-guest interactions are very sensitive to some structural features, such as a neg. charged carboxylate group attached to the ferrocene residue, which may completely disrupt the stability of the complexes.
ER  -

JEON, Woo Sung, Kwangyul MOON, Sang Hyun PARK, Hyungpil CHUN, Young Ho KO, Jin Yong LEE, Eun Sung LEE, S. SAMAL, N. SELVAPALAM, Mikhail V REKHARSKY, Vladimír ŠINDELÁŘ, David SOBRANSINGH, Yoshihisa INOUE, Angel E KAIFER and Kimoon KIM. Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families. \textit{Journal of the American Chemical Society}. Washington, D.C.: American Chemical Society, 2005, vol.~127, No~37, p.~12984-12989. ISSN~0002-7863.

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