A Multifunctional, Charge-Neutral, Chiral Octahedral M12 L12 Cage.

chirality; gas storage; metal-organic cage; self-assembly; supramolecular chemistry; Enantiopure; Fluorescence properties; Internal voids; Large pores; Solid-state structures; Synthesised; Catalysis; Organic Chemistry

Abstract :

[en] A chiral, octahedral M12 L12 cage, which is charge neutral and contains an internal void of about 2000 Å3 , is reported. The cage was synthesised as an enantiopure complex by virtue of amino-acid-based dicarboxylate ligands, which assemble around copper paddlewheels at the vertices of the octahedron. The cage persists in solution with retention of the fluorescence properties of the parent acid. The solid-state structure contains large pores both within and between the cages, and displays permanent porosity for the sorption of gases with retention of crystallinity. Initial tests show some enantioselectivity of the cage towards guests in solution.

Disciplines :

Chemical engineering

Author, co-author :

Boer, Stephanie A ; School of Chemistry, Monash University, Clayton, VIC 3800, Australia

White, Keith F ; School of Molecular Science, La Trobe University, Wodonga, VIC 3690, Australia

Slater, Benjamin ; Barrer Centre, Department of Chemical Engineering, Imperial College London, SW7 2AZ, UK ; CSIRO, Private Bag 10, Clayton South MDC, VIC 3189, Australia

Emerson, Adrian J; School of Chemistry, Monash University, Clayton, VIC 3800, Australia

Knowles, Gregory P ; School of Chemistry, Monash University, Clayton, VIC 3800, Australia

Donald, William A ; School of Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia

Thornton, Aaron W ; CSIRO, Private Bag 10, Clayton South MDC, VIC 3189, Australia

LADEWIG, Bradley Paul ; University of Luxembourg ; Barrer Centre, Department of Chemical Engineering, Imperial College London, SW7 2AZ, UK ; Institute for Micro Process Engineering, Karlsruhe Institute of Technology, 76344, Eggenstein-Leopoldshafen, Germany

Bell, Toby D M ; School of Chemistry, Monash University, Clayton, VIC 3800, Australia

Hill, Matthew R ; CSIRO, Private Bag 10, Clayton South MDC, VIC 3189, Australia ; School of Chemical Engineering, Monash University, Clayton, VIC 3800, Australia

More authors (3 more)

External co-authors :

yes

Language :

English

Title :

A Multifunctional, Charge-Neutral, Chiral Octahedral M12 L12 Cage.

Publication date :

26 June 2019

Journal title :

Chemistry

ISSN :

0947-6539

eISSN :

1521-3765

Publisher :

Wiley-VCH Verlag, Germany

Volume :

Issue :

Pages :

8489 - 8493

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201901681

Funders :

Australian Research Council

Funding text :

Part of this work was conducted on the MX1 beamline at the Australian Synchrotron, part of ANSTO.[23] D.R.T. and M.R.H. acknowledge the Australian Research Council (ARC) for Future Fellowships (FT120100300 and FT130100345), and T.D.M.B. acknowledges the ARC for a Discovery Project (DP170104477). S.A.B. acknowledges the Australian Government for an RTP scholarship. B.S. acknowledges CSIRO and Imperial College London for financial support.

Available on ORBilu :

since 15 January 2024

Statistics

Number of views

49 (1 by Unilu)

Number of downloads

9 (0 by Unilu)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

WoS citations^™

Bibliography

S. J. Dalgarno, N. P. Power, J. L. Atwood, Coord. Chem. Rev. 2008, 252, 825–841;
M. D. Ward, P. R. Raithby, Chem. Soc. Rev. 2013, 42, 1619–1636;
A. Schmidt, A. Casini, F. E. Kuhn, Coord. Chem. Rev. 2014, 275, 19–36.
D. J. L. Tranchemontagne, Z. Ni, M. O'Keeffe, O. M. Yaghi, Angew. Chem. Int. Ed. 2008, 47, 5136–5147;
Angew. Chem. 2008, 120, 5214–5225;
M. D. Ward, Chem. Commun. 2009, 4487–4499;
J. R. Li, H.-C. Zhou, Nat. Chem. 2010, 2, 893–898.
K. Harris, D. Fujita, M. Fujita, Chem. Commun. 2013, 49, 6703–6712;
N. Ahmad, H. A. Younas, A. H. Chughtai, F. Verpoort, Chem. Soc. Rev. 2015, 44, 9–25;
D. Yang, J. Zhao, L. Yu, X. S. Lin, W. Y. Zhang, H. W. Ma, A. Gogoll, Z. B. Zhang, Y. Y. Wang, X. J. Yang, B. Wu, J. Am. Chem. Soc. 2017, 139, 5946–5951.
M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. Int. Ed. 2009, 48, 3418–3438;
Angew. Chem. 2009, 121, 3470–3490;
X. Jing, C. He, Y. Yang, C. Y. Duan, J. Am. Chem. Soc. 2015, 137, 3967–3974;
H. Vardhan, F. Verpoort, Adv. Synth. Catal. 2015, 357, 1351–1368.
J. E. M. Lewis, E. L. Gavey, S. A. Cameron, J. D. Crowley, Chem. Sci. 2012, 3, 778–784;
J. Bunzen, J. Iwasa, P. Bonakdarzadeh, E. Numata, K. Rissanen, S. Sato, M. Fujita, Angew. Chem. Int. Ed. 2012, 51, 3161–3163;
Angew. Chem. 2012, 124, 3215–3217.
J. K. Clegg, J. C. McMurtrie, Chiral Metallosupramolecular Polyhedra in Chirality in Supramolecular Assemblies (Ed.: F. R. Keene), Wiley, Chichester, 2017;
M. Pan, K. Wu, J.-H. Zhang, C.-Y. Su, Coord. Chem. Rev. 2019, 378, 333–349;
A. M. Castilla, W. J. Ramsay, J. R. Nitschke, Acc. Chem. Res. 2014, 47, 2063–2073.
R. A. Bilbeisi, J. K. Clegg, N. Elgrishi, X. De Hatten, M. Devillard, B. Breiner, P. Mal, J. R. Nitschke, J. Am. Chem. Soc. 2012, 134, 5110–5119;
T. F. Liu, Y. Liu, W. M. Xuan, Y. Cui, Angew. Chem. Int. Ed. 2010, 49, 4121–4124;
Angew. Chem. 2010, 122, 4215–4218;
K. Wu, K. Li, Y. J. Hou, M. Pan, L. Y. Zhang, L. Chen, C. Y. Sun, Nat. Commun. 2016, 7, 10487;
W. M. Xuan, M. N. Zhang, Y. Liu, Z. J. Chen, Y. Cui, J. Am. Chem. Soc. 2012, 134, 6904–6907.
S. A. Boer, C. S. Hawes, D. R. Turner, Chem. Commun. 2014, 50, 1125–1127;
S. A. Boer, Y. Nolvachai, C. Kulsing, L. J. McCormick, P. J. Marriott, D. R. Turner, Chem. Eur. J. 2014, 20, 11308–11312;
L. J. McCormick, D. R. Turner, CrystEngComm 2013, 15, 8234–8236;
N. Kyratzis, W. Cao, E. I. Izgorodina, D. R. Turner, CrystEngComm 2018, 20, 4115–4126;
S. A. Boer, D. R. Turner, Cryst. Growth Des. 2016, 16, 6294–6303;
S. A. Boer, R. Cox, M. J. Beards, H. Wang, W. A. Donald, T. D. M. Bell, D. R. Turner, Chem. Commun. 2019, 55, 663–666.
S. Mollick, S. Mukherjee, D. Kim, Q. Zhiwei, A. V. Desai, R. Saha, Y. D. More, J. Jiang, M. S. Lah, S. K. Ghosh, Angew. Chem. Int. Ed. 2019, 58, 1041–1045;
Angew. Chem. 2019, 131, 1053–1057.
T. F. Willems, C. H. Rycroft, M. Kazi, J. C. Meza, M. Haranczyk, Microporous Mesoporous Mater. 2012, 149, 134–141.
A. L. Spek, Acta. Crystallogr. Sect. C 2015, 71, 9–18.
E. P. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data 1998, 27, 413–656.
S. A. Boer, D. R. Turner, Chem. Commun. 2015, 51, 17375–17378.
Z. Lu, C. B. Knobler, H. Furukawa, B. Wang, G. N. Liu, O. M. Yaghi, J. Am. Chem. Soc. 2009, 131, 12532–12533.
G. A. Craig, P. Larpent, S. Kusaka, R. Matsuda, S. Kitagawa, S. Furukawa, Chem. Sci. 2018, 9, 6463–6469;
S. Furukawa, N. Horike, M. Kondo, Y. Hijikata, A. Carné-Sánchez, P. Larpent, N. Louvain, S. Diring, H. Sato, R. Matsuda, R. Kawano, S. Kitagawa, Inorg. Chem. 2016, 55, 10843–10846.
C. A. Rowland, G. R. Lorzing, E. J. Gosselin, B. A. Trump, G. P. A. Yap, C. M. Brown, E. D. Bloch, J. Am. Chem. Soc. 2018, 140, 11153–11157.
J. Park, Z. Perry, Y.-P. Chen, J. Bae, H.-C. Zhou, ACS Appl. Mater. Interfaces 2017, 9, 28064–28068.
M. B. Duriska, S. M. Neville, J. Z. Lu, S. S. Iremonger, J. F. Boas, C. J. Kepert, S. R. Batten, Angew. Chem. Int. Ed. 2009, 48, 8919–8922;
Angew. Chem. 2009, 121, 9081–9084.
K. Sumida, D. L. Rogow, J. A. Mason, T. M. McDonald, E. D. Bloch, Z. R. Herm, T.-H. Bae, J. R. Long, Chem. Rev. 2012, 112, 724–781.
T. D. M. Bell, S. V. Bhosale, C. M. Forsyth, D. Hayne, K. P. Ghiggino, J. A. Hutchison, C. H. Jani, S. J. Langford, M. A.-P. Lee, C. P. Woodward, Chem. Commun. 2010, 46, 4881–4883.
Y. Takashima, V. Martínez Martínez, S. Furukawa, M. Kondo, S. Shimomura, H. Uehara, M. Nakahama, K. Sugimoto, S. Kitagawa, Nat. Commun. 2011, 2, 168.
P. Peluso, V. Mamane, S. Cossu, J. Chromatogr. A 2014, 1363, 11–26;
J. Bojarski, H. Y. Aboul-Enein, A. Ghanem, Curr. Anal. Chem. 2005, 1, 59–77.
N. P. Cowieson, D. Aragao, M. Clift, D. J. Ericsson, C. Gee, S. J. Harrop, N. Mudie, S. Panjikar, J. R. Price, A. Riboldi-Tunnucliffe, R. Williamson, T. Caradoc-Davies, J. Synchrotron Radiat. 2015, 22, 187–190.