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Composition- and Size-Controlled Cyclic Self-Assembly by Solvent- and C60-Responsive Self-Sorting.

Shi, Qixun LU ; Bergquist, Karl-Erik LU ; Huo, Ruiping ; Li, Jilai ; Lund, Mikael LU ; Vácha, Robert ; Sundin, Anders LU ; Butkus, Eugenijus ; Orentas, Edvinas and Wärnmark, Kenneth LU (2013) In Journal of the American Chemical Society 135(40). p.15263-15268
Abstract
Synthesis, solvent-, and guest-controlled self-assembly, and self-sorting of new hydrogen-bonded chiral cavity receptors are reported. The design of the cavity is based on the cyclic self-aggregation of monomers containing the 4H-bonding ureidopyrimidinone motif fused with the bicylo[3.3.1]nonane framework. Selective formation of kinetically inert cyclic tetramers is observed in chloroform, while in toluene an equilibrium between tetrameric and pentameric forms exists. The high affinity of the tetrameric aggregates toward C60 and C70 is observed in aromatic solvents. The host-guest interaction of unconventional π-acidic supramolecular receptors for fullerenes is turned off and on by changing the solvent, whereas the selection of size and... (More)
Synthesis, solvent-, and guest-controlled self-assembly, and self-sorting of new hydrogen-bonded chiral cavity receptors are reported. The design of the cavity is based on the cyclic self-aggregation of monomers containing the 4H-bonding ureidopyrimidinone motif fused with the bicylo[3.3.1]nonane framework. Selective formation of kinetically inert cyclic tetramers is observed in chloroform, while in toluene an equilibrium between tetrameric and pentameric forms exists. The high affinity of the tetrameric aggregates toward C60 and C70 is observed in aromatic solvents. The host-guest interaction of unconventional π-acidic supramolecular receptors for fullerenes is turned off and on by changing the solvent, whereas the selection of size and the very composition of the cavity aggregate is controlled by either the change of solvent or the addition of fullerene guest, making our systems a new type of self-sorting device. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the American Chemical Society
volume
135
issue
40
pages
15263 - 15268
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000326356400053
  • pmid:24067092
  • scopus:84885678512
  • pmid:24067092
ISSN
1520-5126
DOI
10.1021/ja408582w
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Theoretical Chemistry (S) (011001039), Centre for Analysis and Synthesis (011001266)
id
ef0c02d3-5ac0-4208-bafb-d42bbd4e9083 (old id 4065369)
alternative location
http://www.ncbi.nlm.nih.gov/pubmed/24067092?dopt=Abstract
date added to LUP
2016-04-01 10:34:09
date last changed
2020-01-12 04:22:38
@article{ef0c02d3-5ac0-4208-bafb-d42bbd4e9083,
  abstract     = {Synthesis, solvent-, and guest-controlled self-assembly, and self-sorting of new hydrogen-bonded chiral cavity receptors are reported. The design of the cavity is based on the cyclic self-aggregation of monomers containing the 4H-bonding ureidopyrimidinone motif fused with the bicylo[3.3.1]nonane framework. Selective formation of kinetically inert cyclic tetramers is observed in chloroform, while in toluene an equilibrium between tetrameric and pentameric forms exists. The high affinity of the tetrameric aggregates toward C60 and C70 is observed in aromatic solvents. The host-guest interaction of unconventional π-acidic supramolecular receptors for fullerenes is turned off and on by changing the solvent, whereas the selection of size and the very composition of the cavity aggregate is controlled by either the change of solvent or the addition of fullerene guest, making our systems a new type of self-sorting device.},
  author       = {Shi, Qixun and Bergquist, Karl-Erik and Huo, Ruiping and Li, Jilai and Lund, Mikael and Vácha, Robert and Sundin, Anders and Butkus, Eugenijus and Orentas, Edvinas and Wärnmark, Kenneth},
  issn         = {1520-5126},
  language     = {eng},
  number       = {40},
  pages        = {15263--15268},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Journal of the American Chemical Society},
  title        = {Composition- and Size-Controlled Cyclic Self-Assembly by Solvent- and C60-Responsive Self-Sorting.},
  url          = {http://dx.doi.org/10.1021/ja408582w},
  doi          = {10.1021/ja408582w},
  volume       = {135},
  year         = {2013},
}