Enhancement of chemical stability and crystallinity in porphyrin-containing covalent organic frameworks by intramolecular hydrogen bonds

Angewandte Chemie - International Edition

Volumn 52, Issue 49, 2013, Pages 13052-13056

  Kandambeth, Sharath ^a   Shinde, Digambar Balaji ^a   Panda, Manas K ^a   Lukose, Binit ^b   Heine, Thomas ^b   Banerjee, Rahul ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

covalent organic frameworks; hydrogen bonds; mesoporous materials; porphyrinoids; tautomerism

Indexed keywords

COVALENT ORGANIC FRAMEWORKS; CRYSTALLINITIES; HYDROGEN BONDING INTERACTIONS; INTRA-MOLECULAR HYDROGEN BONDS; METHOXY; PORPHYRINOIDS; TAUTOMERISM;

BINDING ENERGY; MESOPOROUS MATERIALS;

HYDROGEN BONDS;

EID: 84888589724     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201306775     Document Type: Article

References (35)

1. A. P. Cote, A. I. Benin, N. W. Ockwig, M. O'Keeffe, A. J. Matzger, O. M. Yaghi, Science 2005, 310, 1166
2. X. Feng, L. Chen, Y. P. Dong, D. Jiang, Chem. Commun. 2011, 47, 1979
3. E. L. Spitler, W. R. Dichtel, Nat. Chem. 2010, 2, 672
4. J. W. Colson, W. R. Dichtel, Nat. Chem. 2013, 5, 453.
5. M. O'Keeffe, B. G. Hyde, Crystal Structures I. Patterns and Symmetry, Mineralogical Society of America, Washington, DC, 1996
6. N. W. Ockwig, O. Delgado-Friedrichs, M. O'Keeffe, O. M. Yaghi, Acc. Chem. Res. 2005, 38, 176.
7. H. Li, M. Eddaoudi, M. O'Keeffe, O. M. Yaghi, Nature 1999, 402, 276
8. C. Janiak, Dalton Trans. 2003, 2781.
9. X. Feng, X. Ding, D. Jiang, Chem. Soc. Rev. 2012, 41, 6010
10. S. Y. Ding, W. Wang, Chem. Soc. Rev. 2013, 42, 548.
11. X. Ding, J. Guo, X. Feng, Y. Honsho, J. Guo, S. Seki, P. Maitarad, A. Saeki, S. Nagase, D. Jiang, Angew. Chem. 2011, 123, 1325
12. Angew. Chem. Int. Ed. 2011, 50, 1289
13. M. Dogru, M. Handloser, F. Auras, T. Kunz, D. Medina, A. Hartschuh, P. Knochel, T. Bein, Angew. Chem. 2013, 125, 2992
14. Angew. Chem. Int. Ed. 2013, 52, 2920
15. S. Wan, J. Guo, J. Kim, H. Ihee, D. Jiang, Angew. Chem. 2008, 120, 8958
16. Angew. Chem. Int. Ed. 2008, 47, 8826
17. X. Feng, L. Liu, Y. Honsho, A. Saeki, S. Seki, S. Irle, Y. Dong, A. Nagai, D. Jiang, Angew. Chem. 2012, 124, 2672
18. Angew. Chem. Int. Ed. 2012, 51, 2618.
19. T. Ben, H. Ren, S. Ma, D. Cao, J. Lan, X. Jing, W. Wang, J. Xu, F. Deng, J. M. Simmons, S. Qiu, G. Zhu, Angew. Chem. 2009, 121, 9621
20. Angew. Chem. Int. Ed. 2009, 48, 9457
21. P. Kuhn, M. Antonietti, A. Thomas, Angew. Chem. 2008, 120, 3499
22. Angew. Chem. Int. Ed. 2008, 47, 3450
23. A. Bhunia, V. Vasylyeva, C. Janiak, Chem. Commun. 2013, 49, 3961.
24. L. M. Lanni, R. W. Tilford, M. Bharathy, J. J. Lavigne, J. Am. Chem. Soc. 2011, 130, 11872
25. Y. Du, K. Mao, P. Kamakoti, P. Ravikovitch, C. Paur, S. Cundy, Q. Li, D. Calabro, Chem. Commun. 2012, 48, 4606.
26. S. Kandambeth, A. Mallick, B. Lukose, N. V. Mane, T. Heine, R. Banerjee, J. Am. Chem. Soc. 2012, 134, 19524.
27. S. Wan, F. Gandara, A. Asano, H. Furukawa, A. Saeki, S. K. Dey, L. Liao, M. W. Ambrogio, Y. Y. Botros, X. Duan, S. Seki, J. F. Stoddart, O. M. Yaghi, Chem. Mater. 2011, 23, 4094.
28. B. Lukose, A. Kuc, T. Heine, Chem. Eur. J. 2011, 17, 2388.
29. B. M. Draškovic̈, G. A. Bogdanovic̈, M. A. Neelakantan, A. C. Chamayou, S. Thalamuthu, Y. S. Avadhut, J. S. Günne, S. Banerjee, C. Janiak, Cryst. Growth Des. 2010, 10, 1665.
30. X. Chen, M. Addicoat, S. Irle, A. Nagai, D. Jiang, J. Am. Chem. Soc. 2013, 135, 546.
31. A. C. Dash, R. K. Nanda, J. Am. Chem. Soc. 1969, 91, 6944
32. P. Di Bernardo, P. L. Zanonato, S. Tamburini, P. Tomasinb, P. A. Vigatob, Dalton Trans. 2006, 4711.
33. G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999
34. A. Kovács, A. Szabõ, I. Hargittai, Acc. Chem. Res. 2002, 35, 887.
35. Y. Xin, J. Yuan, Polym. Chem. 2012, 3, 3045.