CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Australian Journal of Chemistry   
Australian Journal of Chemistry
Journal Banner
  An international journal for chemical science
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Board
Contacts
For Advertisers
Content
Online Early
Current Issue
Just Accepted
All Issues
Virtual Issues
Special Issues
Research Fronts
Sample Issue
Covers
For Authors
General Information
Notice to Authors
Submit Article
Open Access
For Referees
Referee Guidelines
Review Article
For Subscribers
Subscription Prices
Customer Service
Print Publication Dates

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook twitter youtube

Affiliated with RACI

Royal Australian Chemical Institute
Royal Australian
Chemical Institute


 

Article << Previous     |     Next >>   Contents Vol 66(4)

Triazolium-Containing Metal–Organic Frameworks: Control of Catenation in 2D Copper(ii) Paddlewheel Structures

Alexandre Burgun A , Christian J. Doonan A and Christopher J. Sumby A B

A School of Chemistry and Physics, University of Adelaide, Adelaide, SA 5005, Australia.
B Corresponding author. Email: christopher.sumby@adelaide.edu.au

Australian Journal of Chemistry 66(4) 409-418 http://dx.doi.org/10.1071/CH12462
Submitted: 8 October 2012  Accepted: 6 November 2012   Published: 14 December 2012


 
PDF (1.1 MB) $25
 Supplementary Material
 Export Citation
 Print
  
Abstract

One approach to exploit metal–organic frameworks (MOFs) as heterogeneous catalyst platforms requires the development of materials containing groups that can be utilised to anchor a catalytic moiety into the links within the structure. Here we report the synthesis of the first integrated triazolium-containing MOF linker and the first MOFs containing linkers of this type. 1,4-Bis(4-benzoic acid)-1-methyl-1H-1,2,3-triazolium chloride, H2L1Me, was synthesised in three steps by a ‘click’ reaction of methyl 4-ethynylbenzoate with methyl 4-azidobenzoate, methylation using methyl triflate, followed by ester hydrolysis in overall 74 % yield. The equivalent neutral triazole precursor, 1,4-bis(4-benzoic acid)-1H-1,2,3-triazole hydrochloride, H2L1(HCl), was also prepared and a comparison of the chemistry with Zn(NO3)2·6H2O and Cu(NO3)2·3H2O is presented. The results support the use of reaction conditions to control interpenetration and provide additional evidence that the charge on structurally similar ligands can drastically alter the types of structures that are accessible due to the requirements for charge balance in the final product.





References

[1]  (a) S. Kitagawa, R. Kitaura, S.-I. Noro, Angew. Chem. Int. Ed. 2004, 43, 2334.
         | CrossRef | CAS |
      (b) G. Ferey, Chem. Soc. Rev. 2008, 37, 191.
         | CrossRef |
      (c) R. Robson, Dalton Trans. 2008, 5113.
         | CrossRef |
         (d) S. R. Batten, S. M. Neville, D. R. Turner, Coordination Polymers: Design, Analysis and Application 2009, p. 471 (Royal Society of Chemistry: Cambridge).

[2]  (a) M. Eddaoudi, J. Kim, N. L. Rosi, D. T. Vodak, J. Wachter, M. O’Keeffe, O. M. Yaghi, Science 2002, 295, 469.
         | CrossRef | CAS |
      (b) H. Deng, C. J. Doonan, H. Furukawa, R. B. Ferreira, J. Towne, C. B. Knobler, B. Wang, O. M. Yaghi, Science 2010, 327, 846.
         | CrossRef |
      (c) N. Stock, S. Biswas, Chem. Rev. 2012, 112, 933.
         | CrossRef |

[3]  (a) A. Corma, H. Garcia, F. X. Llabres, I. Xamena, Chem. Rev. 2010, 110, 4606.
         | CrossRef | CAS |
      (b) L. Ma, C. Abney, W. Lin, Chem. Soc. Rev. 2009, 38, 1248.
         | CrossRef |
      (c) A. U. Czaja, N. Trukhan, U. Müller, Chem. Soc. Rev. 2009, 38, 1284.
         | CrossRef |
      (d) J. Lee, O. K. Farha, J. Roberts, K. A. Scheidt, S. T. Nguyen, J. T. Hupp, Chem. Soc. Rev. 2009, 38, 1450.
         | CrossRef |

[4]  (a) E. D. Bloch, D. Britt, C. Lee, C. J. Doonan, F. J. Uribe-Romo, H. Furukawa, J. R. Long, O. M. Yaghi, J. Am. Chem. Soc. 2010, 132, 14382.
         | CrossRef | CAS |
      (b) C. J. Doonan, W. Morris, H. Furukawa, O. M. Yaghi, J. Am. Chem. Soc. 2009, 131, 9492.
         | CrossRef |
      (c) T. Jacobs, R. Clowes, A. I. Cooper, M. J. Hardie, Angew. Chem. Int. Ed. 2012, 51, 5192.
         | CrossRef |

[5]  (a) C. Wang, Z. Xie, K. E. deKrafft, W. Lin, J. Am. Chem. Soc. 2011, 133, 13445.
         | CrossRef | CAS |
      (b) P. V. Dau, M. Kim, S. J. Garibay, F. H. L. Muench, C. E. Moore, S. M. Cohen, Inorg. Chem. 2012, 51, 5671.
         | CrossRef |
      (c) P. V. Dau, M. Kim, S. M. Cohen, Chem. Sci. 2013, Advance Article.
         | CrossRef |

[6]  A. J. Nuñez, L. N. Shear, N. Dahal, I. A. Ibarra, J. Yoon, Y. K. Hwang, J.-S. Chang, S. M. Humphrey, Chem. Commun. 2011, 47, 11855.
         | CrossRef |

[7]  (a) J. S. Seo, D. Whang, H. Lee, S. I. Jun, J. Oh, Y. J. Jeon, K. Kim, Nature 2000, 404, 982.
         | CrossRef | CAS |
      (b) B. Chen, L. Wang, Y. Xiao, F. R. Fronczek, M. Xue, Y. Cui, G. Qian, Angew. Chem. Int. Ed. 2009, 48, 500.
         | CrossRef |
      (c) X.-P. Zhou, Z. Xu, M. Zeller, A. D. Hunter, Chem. Commun. 2009, 5439.
         | CrossRef |

[8]  (a) C.-D. Wu, A. Hu, L. Zhang, W. Lin, J. Am. Chem. Soc. 2005, 127, 8940.
         | CrossRef | CAS |
      (b) K. L. Mulfort, O. K. Farha, C. L. Stern, A. A. Sarjent, J. T. Hupp, J. Am. Chem. Soc. 2009, 131, 3866.
         | CrossRef |
      (c) T. Devic, P. Horcajada, C. Serre, F. Salles, G. Maurin, B. Moulin, D. Heurtaux, G. Clet, A. Vimont, J.-M. Greneche, B. Le Ouay, F. Moreau, E. Magnier, Y. Filinchuk, J. Marrot, J.-C. Lavalley, M. Daturi, G. Ferey, J. Am. Chem. Soc. 2010, 132, 1127.
         | CrossRef |
      (d) K. S. Jeong, Y. B. Go, S. M. Shin, S. J. Lee, J. Kim, O. M. Yaghi, N. Jeong, Chem. Sci. 2011, 2, 877.
         | CrossRef |
      (e) D. Rankine, A. Avellaneda, M. R. Hill, C. J. Doonan, C. J. Sumby, Chem. Commun. 2012, 48, 10328.
         | CrossRef |

[9]  (a) Z. Fei, T. D. Geldbach, D. Zhao, R. Scopelliti, P. J. Dyson, Inorg. Chem. 2005, 44, 5200.
         | CrossRef | CAS |
      (b) Z. Fei, T. D. Geldbach, D. Zhao, R. Scopelliti, P. J. Dyson, Inorg. Chem. 2006, 45, 6331.
         | CrossRef |
      (c) L. Han, S. Zhang, Y. Wang, X. Yan, X. Lu, Inorg. Chem. 2009, 48, 786.
         | CrossRef |
      (d) R. S. Crees, M. L. Cole, L. R. Hanton, C. J. Sumby, Inorg. Chem. 2010, 49, 1712.
         | CrossRef |
      (e) J. Chun, I. G. Jung, H. J. Kim, M. Park, M. S. Lah, S. U. Son, Inorg. Chem. 2009, 48, 6353.
         | CrossRef |
      (f) J. Chun, H. S. Lee, I. G. Jung, S. W. Lee, H. J. Kim, S. U. Son, Organometallics 2010, 29, 1518.
         | CrossRef |
      (g) J. Y. Lee, J. Roberts, O. K. Farha, J. T. Hupp, K. A. Scheidt, Inorg. Chem. 2009, 48, 9971.
         | CrossRef |
      (h) G.-Q. Kong, X. Xu, C. Zou, C.-D. Wu, Chem. Commun. 2011, 47, 11005.
         | CrossRef |

[10]  J. M. Roberts, O. K. Farha, A. A. Sarjeant, J. T. Hupp, K. A. Scheidt, Cryst. Growth Des. 2011, 11, 4747.
         | CrossRef | CAS |

[11]  K. Oisaki, Q. Li, H. Furukawa, A. U. Czaja, O. M. Yaghi, J. Am. Chem. Soc. 2010, 132, 9262.
         | CrossRef | CAS |

[12]  (a) J. R. Struble, J. W. Bode, Tetrahedron 2008, 64, 6961.
         | CrossRef | CAS |
      (b) J. R. Struble, J. Kaeobamrung, J. W. Bode, Org. Lett. 2008, 10, 957.
         | CrossRef |

[13]  (a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.
         | CrossRef | CAS |
      (b) J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249.
         | CrossRef |
      (c) M. G. Finn, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1231.
         | CrossRef |

[14]  (a) J. D. Crowley, A.-L. Lee, K. J. Kilpin, Aust. J. Chem. 2011, 64, 1118.
         | CrossRef | CAS |
         (b) J. D. Crowley, D. A. McMorran, in Click Triazoles: Topics in Heterocyclic Chemistry (Ed. J. Košmrlj) 2012, Vol. 28, pp. 31–84 (Springer: Berlin).
      (c) D. Schweinfurth, N. Deibel, F. Weisser, B. Sarkar, Nachr. Chem. 2011, 59, 937.
         | CrossRef |
      (d) H. Struthers, T. L. Mindt, R. Schibli, Dalton Trans. 2010, 39, 675.
         | CrossRef |
      (e) S. O. Scott, E. L. Gavey, S. J. Lind, K. C. Gordon, J. D. Crowley, Dalton Trans. 2011, 40, 12117.
         | CrossRef |
      (f) K. J. Kilpin, U. S. D. Paul, A.-L. Lee, J. D. Crowley, Chem. Commun. 2011, 47, 328.
         | CrossRef |
      (g) K. J. Kilpin, E. L. Gavey, C. J. McAdam, C. B. Anderson, S. J. Lind, C. C. Keep, K. C. Gordon, J. D. Crowley, Inorg. Chem. 2011, 50, 6334.
         | CrossRef |

[15]  V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596.
         | CrossRef | CAS |

[16]  A. R. Katritzky, Y. Zhang, S. K. Singh, Heterocycles 2003, 60, 1225.
         | CrossRef | CAS |

[17]  G. Guisado-Barrios, J. Bouffard, B. Donnadieu, G. Bertrand, Organometallics 2011, 30, 6017.
         | CrossRef | CAS |

[18]  (a) Y. Hua, A. H. Flood, Chem. Soc. Rev. 2010, 39, 1262.
         | CrossRef | CAS |
      (b) A. D. Pehere, C. J. Sumby, A. D. Abell, Org. Biomol. Chem. 2012, Advance Article.
         | CrossRef |

[19]  (a) J. Zhang, L. Wojtas, R. W. Larsen, M. Eddaoudi, M. J. Zaworotko, J. Am. Chem. Soc. 2009, 131, 17040.
         | CrossRef | CAS |
      (b) J. I. Feldblyum, A. G. Wong-Foy, A. J. Matzger, Chem. Commun. 2012, 48, 9828.
         | CrossRef |

[20]  (a) M. Eddaoudi, D. B. Moler, H. Li, B. Chen, T. M. Reineke, M. O’Keeffe, O. M. Yaghi, Acc. Chem. Res. 2001, 34, 319.
         | CrossRef | CAS |
      (b) D. J. Tranchemontagne, J. L. Mendoza-Cortés, M. O’Keeffe, O. M. Yaghi, Chem. Soc. Rev. 2009, 38, 1257.
         | CrossRef |

[21]  A. L. Spek, Acta Crystallogr. 1990, A46, C34.

[22]  W. B. Austin, N. Bilow, W. J. Kelleghan, K. S. Y. Lau, J. Org. Chem. 1981, 46, 2280.
         | CrossRef | CAS |

[23]  M. Tanno, S. Sueyoshi, S. Kamiya, Chem. Pharm. Bull. (Tokyo) 1982, 30, 3125.
         | CrossRef | CAS |

[24]  T. M. McPhillips, S. E. McPhillips, H. J. Chiu, A. E. Cohen, A. M. Deacon, P. J. Ellis, E. Garman, A. Gonzalez, N. K. Sauter, R. P. Phizackerley, S. M. Soltis, P. Kuhn, J. Synchrotron Radiat. 2002, 9, 401.
         | CrossRef | CAS |

[25]  G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467.
         | CAS |

[26]  G. M. Sheldrick, SHELXL-97 1997 (University of Göttingen: Göttingen).

[27]  L. J. Barbour, J. Supramol. Chem. 2001, 1, 189.
         | CrossRef | CAS |

[28]  Persistence of Vision Raytracer Pty Ltd, POV-Ray, Williamstown, Australia, 20032008.

[29]  G. M. Sheldrick, CIFTAB 1997 (University of Göttingen: Göttingen).

[30]  P. Gilli, L. Pretto, V. Bertolasi, G. Gilli, Acc. Chem. Res. 2009, 42, 33.
         | CrossRef | CAS |


   
Subscriber Login
Username:
Password:  

 


    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2014