The pi-stacking interaction between shape-persistent cyclophanes works cooperatively with multiple hydrogen bonding sites to form cyclophane dimers. These findings considerably broaden the applicability of pi-stacking interactions as a driving force in self-assembly chemistry. A gel formation effect was also noticed in one of the cyclophanes.
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http://dx.doi.org/10.1021/jo025723a | DOI Listing |
Chemistry
March 2024
Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S C Mullick Road, Kolkata, 700032, India.
Water-soluble organic cages are attractive targets for their molecular recognition and sensing features of biologically relevant molecules. Here, we have successfully designed and synthesized a pair of water-soluble cationic cages employing click reaction as the fundamental step followed by the N-methylation of the triazole rings. The rigid and shape-persistent 3D hydrophobic cavity, positively charged surface, H-bonding triazolium rings, and excellent water solubility empower both cages to exhibit a superior affinity and selectivity for binding with adenosine-5'-triphosphate (ATP) compared to cyclophanes and other macrocyclic receptors.
View Article and Find Full Text PDFChemistry
August 2015
Departamento de Química Orgánica, Universidade de Vigo, Lagoas-Marcosende, 36310, Vigo (Spain).
A combined experimental-computational analysis of the one- and two-photon absorption (OPA, TPA) and the electronic circular dichroism (ECD) of complex chiral shape-persistent (2,6)-pyrido[142 ]allenoacetylenic cyclophane, (P,P,P,P)-MC[142 ] enantiomers, sheds light on the origin of their peculiar spectral signatures. The study on MC[142 ], which is represented in solution by three possible conformers, indicates that two of them (chair and twist) are the prevalent conformers at room temperature; the population ratio depending on the solvent. The complex shape of the red-edge of the UV and ECD spectra is qualitatively reproduced by using vibronic calculations and assigned to progressions on the ethynyl stretchings observable only in the chair and twist conformers.
View Article and Find Full Text PDFChirality
September 2014
Organic Chemistry Department, Universidade de Vigo, Vigo, Spain.
The design and synthesis of chiral cyclophanes containing signaling functional groups as an integral part of the macrocyclic framework offer promising possibilities for chiral sensing, molecular recognition, and chiral supramolecular architectures. Our research group has been involved in the construction and study of chiroptical properties of several allenic meta- and para-cyclophanes bearing anthracene and pyridine rings as spacers. A revision of our results is presented.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2005
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI, 8093 Zurich, Switzerland.
J Org Chem
November 2002
Department of Chemistry and Center for Nanoscale Science and Technology, MS 222, Rice University, 6100 Main Street, Houston, Texas 77005, USA.
The pi-stacking interaction between shape-persistent cyclophanes works cooperatively with multiple hydrogen bonding sites to form cyclophane dimers. These findings considerably broaden the applicability of pi-stacking interactions as a driving force in self-assembly chemistry. A gel formation effect was also noticed in one of the cyclophanes.
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