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

Angewandte Chemie - International Edition - Tập 45 Số 6 - Trang 916-920 - 2006
Danil N. Dybtsev1,2,3, Alexey L. Nuzhdin4, Hyungphil Chun1,2, Konstantin P. Bryliakov4, Evgenii P. Talsi4, Vladimir P. Fedin3, Kimoon Kim1,2
1Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31 Hyojadong, Pohang 790-784, Republic of Korea, Fax: (+82) 54-279-8129
2National Creative Research Initiative Center for Smart, Supramolecules
3Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, Pr. Lavrentieva 3, Novosibirsk 630090, Russia, Fax: (+7) 383-330-9489
4Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Pr. Lavrentieva, 5, Novosibirsk 630090, Russia

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Tài liệu tham khảo

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.

 

10.1002/1521-3757(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

2005, Angew. Chem. Int. Ed., 44, 5472

Guillou N., 2003, Angew. Chem., 115, 4137

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