Structural Insight into Guest Binding Sites in a Porous Homochiral Metal-Organic Material

Journal of the American Chemical Society
Shi-Yuan ZhangMichael J Zaworotko

Abstract

An enantiomeric pair of chiral metal-organic materials (CMOMs) based upon mandelate (man) and 4,4'-bipyridine (bpy) ligands, [Co2(S-man)2(bpy)3](NO3)2·guest (1S·guest) and [Co2(R-man)2(bpy)3](NO3)2·guest (1R·guest), have been prepared. The cationic frameworks exhibit one-dimensional chiral channels with dimensions of 8.0 Å × 8.0 Å. The pore chemistry is such that chiral surfaces lined with nitrate anions and phenyl groups create multiple binding sites for guest and/or solvent molecules. The performance of 1S and 1R with respect to resolution of racemic mixtures of 1-phenyl-1-propanol (PP) was studied by varying time, temperature, and the use of additives. Selectivity toward PP was determined by chiral HPLC with ee values of up to 60%. The binding sites and host-guest interactions were investigated through single-crystal X-ray structural analyses of guest-exchanged 1S and 1R. Crystallographically observed structural changes (e.g., the absolute configurations of the three PP binding sites switch from R, R, and S to R, R, and R/S) correlate with experimentally observed ee values of 33% and 60% for variants of 1S that contain PP and different solvent molecules, 1S·PPex and 1S·PPex', respectively. The fact that manipulation of guest...Continue Reading

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Citations

Jan 28, 2016·Journal of the American Chemical Society·Karel J HartliebJ Fraser Stoddart
Nov 26, 2015·Journal of the American Chemical Society·Shi-Yuan ZhangMichael J Zaworotko
Apr 27, 2016·Journal of the American Chemical Society·Feng LuoBanglin Chen
Jun 20, 2016·Journal of Chromatography. a·Gerhard K E Scriba
May 12, 2017·Chemical Communications : Chem Comm·Donata AsnaghiMir Wais Hosseini
Nov 3, 2016·Chemistry : a European Journal·Tanya K TodorovaCaroline Mellot-Draznieks
Jan 24, 2017·Chemical Communications : Chem Comm·Bai-Qiao SongZhong-Min Su
May 29, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Zheng CuiJingping Zhang
Jun 6, 2018·Chemical Communications : Chem Comm·Rosaria BrunoDonatella Armentano
Nov 30, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Hannah L DaltonThorfinnur Gunnlaugsson
Jun 6, 2019·Chemical Communications : Chem Comm·Benjamin SlaterBradley P Ladewig
Dec 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Wen MaXiaoying Huang
Nov 23, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Yun-Shan XueYan Xu
Jun 27, 2020·Angewandte Chemie·Shi-Yuan ZhangMichael J Zaworotko
Apr 2, 2021·ACS Central Science·Ashley D Cardenal, Timothy R Ramadhar
May 12, 2021·Chemical Society Reviews·Juan LiuJian Zhang
Aug 4, 2021·ACS Applied Materials & Interfaces·Zhen-Zhang WengLan-Sun Zheng
Sep 11, 2018·Journal of the American Chemical Society·Shi-Yuan ZhangMichael J Zaworotko
Jul 18, 2018·Inorganic Chemistry·Anees AbbasYong Cui
Aug 8, 2017·Journal of the American Chemical Society·KaKing YanMakoto Fujita
Jan 6, 2018·Journal of the American Chemical Society·Xing HanYong Cui
Nov 29, 2017·Journal of the American Chemical Society·Benjamin SlaterBradley P Ladewig

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