DOI: 10.1002/anie.200503023. A Homochiral Metal–Organic Material with Permanent Porosity, Enantioselective Sorption Properties, and Catalytic Activity

A Homochiral Metal–Organic Material with Permanent Porosity, Enantioselective Sorption Properties, and Catalytic Activity

10.1002/anie.200503023

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Dybtsev, D. N., Nuzhdin, A. L., Chun, H., Bryliakov, K. P., Talsi, E. P., Fedin, V. P., & Kim, K. (2006). A Homochiral MetalâOrganic Material with Permanent Porosity, Enantioselective Sorption Properties, and Catalytic Activity. Angewandte Chemie International Edition, 45(6), 916â920. Portico.

Authors 7

Danil N. Dybtsev (first)
Alexey L. Nuzhdin (additional)
Hyungphil Chun (additional)
Konstantin P. Bryliakov (additional)
Evgeniy P. Talsi (additional)
Vladimir P. Fedin (additional)
Kimoon Kim (additional)

References 94 Referenced 616

Recent reviews on porous metal–organic frameworks:
10.1002/ange.200300610
10.1002/anie.200300610
10.1002/ange.200300588
10.1002/anie.200300588
10.1002/anie.200300636
10.1039/b200393g
10.1039/b305705b
10.1039/b416425c
10.1002/ange.200462786
10.1002/anie.200462786
10.1021/ar040174b
10.1021/ar020022l
10.1021/ar0401606
10.1021/ar040163i
Special issue ofJ. Solid State Chem.2005 178 2409–2573. (10.1016/j.jssc.2005.05.034)
10.1002/1521-3757(20000616)112:12<2161::AID-ANGE2161>3.0.CO;2-6
10.1002/1521-3773(20000616)39:12<2081::AID-ANIE2081>3.0.CO;2-A
10.1126/science.1067208
10.1021/jp0130416
10.1039/B308903G
10.1021/ja049408c
10.1002/ange.200460712
10.1002/anie.200460712
10.1002/chem.200401201
10.1002/ange.200462787
10.1002/anie.200462787
10.1021/ja043756x
10.1038/nature03852
10.1126/science.1101982
10.1002/ange.200460592
10.1002/anie.200460592
10.1002/1521-3765(20010105)7:1<303::AID-CHEM303>3.0.CO;2-H
10.1002/1521-3765(20020816)8:16<3586::AID-CHEM3586>3.0.CO;2-K
10.1021/ja038678c
10.1021/ja0316420
10.1021/ja0523082
10.1002/ange.200453923
10.1002/anie.200453923
10.1021/ar040173j
10.1002/1521-3757(20011203)113:23<4554::AID-ANGE4554>3.0.CO;2-A
10.1002/1521-3773(20011203)40:23<4422::AID-ANIE4422>3.0.CO;2-G
For other applications including magnetism nonlinear optics luminescence sensors conductivity ion‐exchange see comprehensive reviews [1a e] and selected recent papers:
10.1016/j.micromeso.2003.05.001
10.1002/ange.200500717
{'key': 'e_1_2_3_38_3', 'first-page': '5472', 'volume': '44', 'year': '2005', 'journal-title': 'Angew. Chem. Int. Ed.'} / Angew. Chem. Int. Ed. (2005)
{'key': 'e_1_2_3_39_2', 'first-page': '4137', 'volume': '115', 'author': 'Guillou N.', 'year': '2003', 'journal-title': 'Angew. Chem.'} / Angew. Chem. by Guillou N. (2003)
10.1002/anie.200352520
10.1016/j.micromeso.2003.12.029
10.1002/ejic.200400395
10.1126/science.1075948
10.1021/ja00082a055
10.1038/35010088
10.1021/ja052431t
10.1021/ja0163772
10.1021/ja001140b
10.1039/B406114B
10.1016/j.cct.2003.08.004
10.1038/nature00785
For some homochiral metal–organic frameworks the porosity has been demonstrated either by reversible gas sorption or guest inclusion; see refs. [3d h] [5b–d] and
10.1039/b505916j
10.1002/ange.200462711
10.1002/anie.200462711
10.1021/ja029926s
10.1021/ja993814s
Our approach is based on the concept of the SBU which was developed by Yaghi O'Keeffe and co‐workers (see reference [1c]) and has been widely used in the synthesis of metal–organic frameworks. Note that the framework‐forming reaction does not necessarily proceed in a stepwise manner as it appears in Scheme 1. The strategy itself may not be novel but this is the first time that it has been successfully applied in the synthesis of 3D homochiral metal–organic porous materials.
10.1002/ange.200351595
10.1002/anie.200351595
The Zn–O distances between Zn2+ions and the hydroxy oxygen atom of the lactate anion in1(1.969 and 1.939 Å) clearly support the deprotonation of the OH group.
10.1021/ja045123o
10.1002/ange.200353139
10.1002/anie.200353139
10.1038/nature02311
A. L. Spek PLATON a multipurpose crystallographic tool Utrecht University Utrecht The Netherlands 2001.
Recent reviews on chiral sulfoxides:
10.1002/0471721506.ch10
10.1021/cr990372u
10.1002/chir.10274
10.1002/ange.200460108
10.1002/anie.200460108
The material [Zn2(bdc)(L‐lac)(dmf)x] (x<1) with partially removed coordinating DMF ligands showed poorer sorption of3 b(about 0.05 molecules per formula unit of [Zn2(bdc)(L‐lac)(dmf)]) along with a lowereevalue (12 % in favor of theSenantiomer).
After the sorption experiment the crystalline material1was washed thoroughly with CH2Cl2(5 portions 4–5 mL each) to remove traces of sorbed sulfoxide collected by filtration and dried in air for 1 h before use in the next cycles of sorption experiments. The amount of sorbed3 bin1in the second cycle was found to be the same 0.18 molecules per formula unit of [Zn2(bdc)(L‐lac)(dmf)].
The heterogeneous nature of the catalysis was further confirmed in that no conversion was observed in the reaction of2 bwith UHP in the supernatant solution removed after stirring with1in CH2Cl2for 16 h.
10.1016/S0040-4039(00)60849-3
To better understand the mechanism of the catalytic reaction with1 we are also investigating the same reaction using an analogous homogeneous catalyst.
10.1002/ange.200352635
10.1002/anie.200352635
10.1002/ange.200460236
10.1002/anie.200460236

Dates

Type	When
Created	19 years, 7 months ago (Dec. 30, 2005, 4:49 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 7:38 p.m.)
Indexed	1 month, 4 weeks ago (June 23, 2025, 10:24 a.m.)
Issued	19 years, 6 months ago (Jan. 23, 2006)
Published	19 years, 6 months ago (Jan. 23, 2006)
Published Online	19 years, 6 months ago (Jan. 23, 2006)
Published Print	19 years, 6 months ago (Jan. 30, 2006)

Funders 0

None

BibTeX

@article{Dybtsev_2006, title={A Homochiral Metal–Organic Material with Permanent Porosity, Enantioselective Sorption Properties, and Catalytic Activity}, volume={45}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200503023}, DOI={10.1002/anie.200503023}, number={6}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Dybtsev, Danil N. and Nuzhdin, Alexey L. and Chun, Hyungphil and Bryliakov, Konstantin P. and Talsi, Evgeniy P. and Fedin, Vladimir P. and Kim, Kimoon}, year={2006}, month=jan, pages={916–920} }

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      "unstructured": "The material [Zn2(bdc)(L\u2010lac)(dmf)x] (x<1) with partially removed coordinating DMF ligands showed poorer sorption of3\u2009b(about 0.05 molecules per formula unit of [Zn2(bdc)(L\u2010lac)(dmf)]) along with a lowereevalue (12\u2009% in favor of theSenantiomer)."
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      "unstructured": "The heterogeneous nature of the catalysis was further confirmed in that no conversion was observed in the reaction of2\u2009bwith UHP in the supernatant solution removed after stirring with1in CH2Cl2for 16 h."
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