A Remarkably Complex Supramolecular Hydrogen-Bonded Decameric Capsule Formed from an Enantiopure C2-Symmetric Monomer by Solvent-Responsive Aggregation.
(2015) In Journal of the American Chemical Society 137(33). p.10536-10546- Abstract
- The formation of an unprecedented decameric capsule in carbon disulfide, held together by the combination of double and triple hydrogen bonds between isocytosine units embedded in an enantiomerically pure bicyclic framework is reported. The aggregation occurs via symmetry breaking of the enantiopure intrinsically C2-symmetric monomer brought about by solvent, induced tautomerization of the hydrogen-bonding unit. We show that the topology of the aggregate is responsive to the solvent in which the assembly takes place. In this study we demonstrate that in carbon disulfide the chiral decameric cavity aggregate consisting of three forms of the same monomer, differing in their hydrogen bonding to each other is selectively formed, representing a... (More)
- The formation of an unprecedented decameric capsule in carbon disulfide, held together by the combination of double and triple hydrogen bonds between isocytosine units embedded in an enantiomerically pure bicyclic framework is reported. The aggregation occurs via symmetry breaking of the enantiopure intrinsically C2-symmetric monomer brought about by solvent, induced tautomerization of the hydrogen-bonding unit. We show that the topology of the aggregate is responsive to the solvent in which the assembly takes place. In this study we demonstrate that in carbon disulfide the chiral decameric cavity aggregate consisting of three forms of the same monomer, differing in their hydrogen bonding to each other is selectively formed, representing a tube-like structure capped with two C2-symmetric monomers. The large cylindrical cavity produced selectively accommodates one partially solvated C60 molecule, and molecular dynamic simulations revealed the special role of the solvent in the inclusion mechanism. The strategy described herein represents the first step toward the creation of a new class of hydrogen-bonded tubular objects from only one small symmetric building block by solvent-responsive aggregation. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/5456742
- author
- Račkauskaitė, Dovilė ; Bergquist, Karl-Erik LU ; Shi, Qixun LU ; Sundin, Anders LU ; Butkus, Eugenijus ; Wärnmark, Kenneth LU and Orentas, Edvinas
- organization
- publishing date
- 2015
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of the American Chemical Society
- volume
- 137
- issue
- 33
- pages
- 10536 - 10546
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- pmid:25950402
- wos:000360321100024
- pmid:25950402
- scopus:84941671323
- ISSN
- 1520-5126
- DOI
- 10.1021/jacs.5b03160
- language
- English
- LU publication?
- yes
- id
- ea0b02d2-6c3e-4b4c-ab0f-555846f273bc (old id 5456742)
- date added to LUP
- 2016-04-01 09:52:12
- date last changed
- 2022-01-25 17:24:28
@article{ea0b02d2-6c3e-4b4c-ab0f-555846f273bc,
abstract = {{The formation of an unprecedented decameric capsule in carbon disulfide, held together by the combination of double and triple hydrogen bonds between isocytosine units embedded in an enantiomerically pure bicyclic framework is reported. The aggregation occurs via symmetry breaking of the enantiopure intrinsically C2-symmetric monomer brought about by solvent, induced tautomerization of the hydrogen-bonding unit. We show that the topology of the aggregate is responsive to the solvent in which the assembly takes place. In this study we demonstrate that in carbon disulfide the chiral decameric cavity aggregate consisting of three forms of the same monomer, differing in their hydrogen bonding to each other is selectively formed, representing a tube-like structure capped with two C2-symmetric monomers. The large cylindrical cavity produced selectively accommodates one partially solvated C60 molecule, and molecular dynamic simulations revealed the special role of the solvent in the inclusion mechanism. The strategy described herein represents the first step toward the creation of a new class of hydrogen-bonded tubular objects from only one small symmetric building block by solvent-responsive aggregation.}},
author = {{Račkauskaitė, Dovilė and Bergquist, Karl-Erik and Shi, Qixun and Sundin, Anders and Butkus, Eugenijus and Wärnmark, Kenneth and Orentas, Edvinas}},
issn = {{1520-5126}},
language = {{eng}},
number = {{33}},
pages = {{10536--10546}},
publisher = {{The American Chemical Society (ACS)}},
series = {{Journal of the American Chemical Society}},
title = {{A Remarkably Complex Supramolecular Hydrogen-Bonded Decameric Capsule Formed from an Enantiopure C2-Symmetric Monomer by Solvent-Responsive Aggregation.}},
url = {{http://dx.doi.org/10.1021/jacs.5b03160}},
doi = {{10.1021/jacs.5b03160}},
volume = {{137}},
year = {{2015}},
}