Unexpected narcissistic self-sorting at molecular and supramolecular levels in racemic chiral calixsalens?
CrystEngComm Pub Date: 2016-03-17 DOI: 10.1039/C6CE00256K
Abstract
The [3 + 3] cyclocondensation of 2-hydroxyisophthalaldehyde derivatives with racemic trans-1,2-diaminocyclohexane results in formation of triangular vase-like hexaimines called calixsalens. Calixsalen formation is highly stereoselective, yielding racemic mixtures that contain homochiral products with absolute configuration of either all-R or all-S at their stereogenic centres. Calixsalens form tail-to-tail dimers that are assembled into higher-order structures in the solid state. The formation of these dimers is accomplished by enantioselective self-recognition of chiral calixsalen units driven by non-covalent interactions only.
Recommended Literature
- [1] Enabling chloride salts for thermal energy storage: implications of salt purity? J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. MayesRSC Adv., 2019,9, 25602-25608 10.1039/C9RA03133B
- [2] Evolution study of photo-synthesized gold nanoparticles by spectral deconvolution model: a quantitative approach Chung-Sung Yang,Mong-Shian Shih,Fang-Yi ChangNew J. Chem., 2006,30, 729-735 10.1039/B516465F
- [3] Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration? Ziyang Deng,Changwei Chen,Sunliang CuiRSC Adv., 2016,6, 93753-93755 10.1039/C6RA20007A
- [4] Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature Hanie Hashtroudi,Ian D. R. MackinnonJ. Mater. Chem. C, 2020,8, 13108-13126 10.1039/D0TC01968B
- [5] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [6] Fate of single walled carbon nanotubes in wetland ecosystems? Joseph H. Bisesi,Tara Sabo-AttwoodEnviron. Sci.: Nano, 2014,1, 574-583 10.1039/C4EN00063C
- [7] Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples? Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu JunkangNew J. Chem., 2015,39, 5240-5248 10.1039/C5NJ00831J
- [8] Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions? Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng CaiChem. Commun., 2013,49, 11086-11088 10.1039/C3CC46560H
- [9] Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents Craig A. Kelly,David R. RosseinskyPhys. Chem. Chem. Phys., 2001,3, 2086-2090 10.1039/B010092G
- [10] Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage? M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. KaskelJ. Mater. Chem. A, 2015,3, 17983-17990 10.1039/C5TA03730A
Journal Name：CrystEngComm
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)