Inorganic Chemistry
Article
Materials Based on an Amino Acid Backbone. Angew. Chem., Int. Ed.
crystals, monolayers and macro- and supra-molecular polymers and
assemblies. Chem. Soc. Rev. 2007, 36, 941−967.
2
(
006, 45, 6495−6499.
12) Suh, K.; Yutkin, M. P.; Dybtsev, D. N.; Fedin, V. P.; Kim, K.
(31) He, C.; Zhao, Y.; Guo, D.; Lin, Z.; Duan, C. Chirality Transfer
through Helical Motifs in Coordination Compounds. Eur. J. Inorg.
Chem. 2007, 2007, 3451−3463.
Enantioselective sorption of alcohols in a homochiral metal-organic
framework. Chem. Commun. 2012, 48, 513−515.
(
13) Wang, M.; Xie, M.-H.; Wu, C.-D.; Wang, Y.-G. From one to
(32) Serre, C.; Mellot-Draznieks, C.; Surble,
́
S.; Audebrand, N.;
́
ey, G. Role of Solvent-Host Interactions That Lead
three: a serine derivate manipulated homochiral metal-organic
Filinchuk, Y.; Fer
framework. Chem. Commun. 2009, 2396−2398.
to Very Large Swelling of Hybrid Frameworks. Science 2007, 315,
1828−1831.
(
14) Ingleson, M. J.; Barrio, J. P.; Bacsa, J.; Dickinson, C.; Park, H.;
Rosseinsky, M. J. Generation of a solid Bronsted acid site in a chiral
(33) Mahata, P.; Draznieks, C.-M.; Roy, P.; Natarajan, S. Solid State
and Solution Mediated Multistep Sequential Transformations in
Metal−Organic Coordination Networks. Cryst. Growth Des. 2013, 13,
155−168.
framework. Chem. Commun. 2008, 1287−1289.
(
15) Nagaraja, C. M.; Haldar, R.; Maji, T. K.; Rao, C. N. R. Chiral
Porous Metal−Organic Frameworks of Co(II) and Ni(II): Synthesis,
Structure, Magnetic Properties, and CO2 Uptake. Cryst. Growth Des.
(34) Choudhury, A.; Neeraj, S.; Natarajan, S.; Rao, C. N. R.
Transformations of the low-dimensional zinc phosphates to complex
open-framework structures. Part 2:one-dimensional ladder to two- and
three-dimensional structures. J. Mater. Chem. 2001, 11, 1537−1546.
(35) Mandal, S.; Natarajan, S. Synthesis, Structure, and Poly-
morphism Studies in Amine-Templated Open-Framework Zinc
Phosphites. Inorg. Chem. 2008, 47, 5304−5313.
2
(
012, 12, 975−981.
16) Kathalikkattil, A. C.; Bisht, K. K.; Aliaga-Alcalde, N.; Suresh, E.
Synthesis, Magnetic Properties, and Structural Investigation of Mixed-
Ligand Cu(II) Helical Coordination Polymers with an Amino Acid
Backbone and N-Donor Propping: 1-D Helical, 2-D Hexagonal Net
(
1
hcb), and 3-D ins Topologies. Cryst. Growth Des. 2011, 11, 1631−
641.
17) Bisht, K. K.; Suresh, E. Spontaneous Resolution of a Mixed-
(36) Chughtai, A. H.; Ahmad, N.; Younus, H. A.; Laypkov, A.;
Verpoort, F. Metal-organic frameworks: versatile heterogeneous
catalysts for efficient catalytic organic transformations. Chem. Soc.
Rev. 2015, 44, 6804−6849.
(
Ligand Nickel(II) Coordination Polymer with Achiral Precursors.
Inorg. Chem. 2012, 51, 9577−9579.
(37) Halcrow, M. A. Jahn-Teller distortions in transition metal
(
18) Perez-Garcia, L.; Amabilino, D. B. Spontaneous resolution
compounds, and their importance in functional molecular and
under supramolecular control. Chem. Soc. Rev. 2002, 31, 342−356.
inorganic materials. Chem. Soc. Rev. 2013, 42, 1784−1795.
(
19) Liu, Q.-Y.; Wang, Y.-L.; Zhang, N.; Jiang, Y.-L.; Wei, J.-J.; Luo,
(38) SMART (V 5.628), SAINT (V 6.45a), XPREP, SHELXTL;
F. Spontaneous Resolution in the Ionothermal Synthesis of
Homochiral Zn(II) Metal−Organic Frameworks with (10,3)-a Top-
ology Constructed from Achiral 5-Sulfoisophthalate. Cryst. Growth Des.
Bruker AXS Inc.: Madison, WI, 2004.
39) Sheldrick, G. M. Siemens Area Correction Absorption Correction
Program; University of Gottingen: Gottingen, Germany, 1994.
40) Sheldrick, G. M. SHELXL-97: Program for Crystal Structure
Solution and Refinement; University of Gottingen: Gottingen, Germany,
997.
41) Farrugia, L. WinGX suite for small-molecule single-crystal
crystallography. J. Appl. Crystallogr. 1999, 32, 837−838.
42) Blatov, V. A.; Proserpio, D. M. Topological relations between
(
̈
̈
2
(
011, 11, 3717−3720.
(
20) Gao, E.-Q.; Yue, Y.-F.; Bai, S.-Q.; He, Z.; Yan, C.-H. From
̈
̈
Achiral Ligands to Chiral Coordination Polymers: Spontaneous
Resolution, Weak Ferromagnetism, and Topological Ferrimagnetism.
J. Am. Chem. Soc. 2004, 126, 1419−1429.
1
(
(
21) Zheng, X.-D.; Zhang, M.; Jiang, L.; Lu, T.-B. A pair of 3D
(
homochiral metal-organic frameworks: spontaneous resolution, single-
crystal-to-single-crystal transformation and selective adsorption
properties. Dalton Trans. 2012, 41, 1786−1791.
three-periodic nets. II. Binodal nets. Acta Crystallogr., Sect. A: Found.
Crystallogr. 2009, 65, 202−212.
(43) Ma, L.; Abney, C.; Lin, W. Enantioselective catalysis with
(
22) Tong, X.-L.; Hu, T.-L.; Zhao, J.-P.; Wang, Y.-K.; Zhang, H.; Bu,
homochiral metal-organic frameworks. Chem. Soc. Rev. 2009, 38,
248−1256.
44) Yoon, M.; Srirambalaji, R.; Kim, K. Homochiral Metal−Organic
Frameworks for Asymmetric Heterogeneous Catalysis. Chem. Rev.
012, 112, 1196−1231.
X.-H. Chiral magnetic metal-organic frameworks of MnII with achiral
tetrazolate-based ligands by spontaneous resolution. Chem. Commun.
1
(
2
(
010, 46, 8543−8545.
23) Yang, Q.; Chen, Z.; Hu, J.; Hao, Y.; Li, Y.; Lu, Q.; Zheng, H. A
2
second-order nonlinear optical material with a hydrated homochiral
helix obtained via spontaneous symmetric breaking crystallization from
an achiral ligand. Chem. Commun. 2013, 49, 3585−3587.
(
45) Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. Metal−Organic
Frameworks as Efficient Heterogeneous Catalysts for the Regiose-
lective Ring Opening of Epoxides. Chem. - Eur. J. 2010, 16, 8530−
(
24) Wu, S.-T.; Wu, Y.-R.; Kang, Q.-Q.; Zhang, H.; Long, L.-S.;
8
536.
Zheng, Z.; Huang, R.-B.; Zheng, L.-S. Chiral Symmetry Breaking by
Chemically Manipulating Statistical Fluctuation in Crystallization.
Angew. Chem., Int. Ed. 2007, 46, 8475−8479.
(
́ ́
46) Corma, A.; Iglesias, M.; Llabres i Xamena, F. X.; Sanchez, F. Cu
and Au Metal−Organic Frameworks Bridge the Gap between
Homogeneous and Heterogeneous Catalysts for Alkene Cyclo-
propanation Reactions. Chem. - Eur. J. 2010, 16, 9789−9795.
(
25) Kepert, C. J.; Prior, T. J.; Rosseinsky, M. J. A Versatile Family of
Interconvertible Microporous Chiral Molecular Frameworks: The First
Example of Ligand Control of Network Chirality. J. Am. Chem. Soc.
(47) Elassar, A.-Z. A.; El-Khair, A. A. Recent developments in the
chemistry of enaminones. Tetrahedron 2003, 59, 8463−8480.
2
(
000, 122, 5158−5168.
26) Zhang, J.; Bu, X. Absolute helicity induction in three-
dimensional homochiral frameworks. Chem. Commun. 2009, 206−208.
(48) Salama, N. N.; Scott, K. R.; Eddington, N. D. DM27, an
enaminone, modifies the in vitro transport of antiviral therapeutic
agents. Biopharm. Drug Dispos. 2004, 25, 227−236.
(
27) Dang, D.; Wu, P.; He, C.; Xie, Z.; Duan, C. Homochiral Metal−
(
́
49) Luz, I.; Llabres i Xamena, F. X.; Corma, A. Bridging
Organic Frameworks for Heterogeneous Asymmetric Catalysis. J. Am.
Chem. Soc. 2010, 132, 14321−14323.
(
homogeneous and heterogeneous catalysis with MOFs: “Click”
reactions with Cu-MOF catalysts. J. Catal. 2010, 276, 134−140.
́
28) Degenbeck, H.; Felten, A.-S.; Escudero-Adan, E. C.; Benet-
Buchholz, J.; Di Bari, L.; Pescitelli, G.; Vidal-Ferran, A. New Chiral
Zinc Complexes: Synthesis, Structure, and Induction of Axial Chirality.
Inorg. Chem. 2012, 51, 8643−8645.
(
29) Kondepudi, D. K.; Kaufman, R. J.; Singh, N. Chiral Symmetry
Breaking in Sodium Chlorate Crystallizaton. Science 1990, 250, 975−
76.
30) Perez-Garcia, L.; Amabilino, D. B. Spontaneous resolution,
whence and whither: from enantiomorphic solids to chiral liquid
9
(
F
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