Tandem Synthesis of Photoactive Benzodifuran Moieties in the Formation of Microporous Organic Networks†
Narae Kang
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorDr. Ji Hoon Park
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorKyoung Chul Ko
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorJiseul Chun
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorEunchul Kim
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorDr. Hee-Won Shin
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorDr. Sang Moon Lee
Korea Basic Science Institute, Daejeon 350-333 (Korea)
Search for more papers by this authorDr. Hae Jin Kim
Korea Basic Science Institute, Daejeon 350-333 (Korea)
Search for more papers by this authorCorresponding Author
Prof. Tae Kyu Ahn
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)Search for more papers by this authorCorresponding Author
Prof. Jin Yong Lee
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)Search for more papers by this authorCorresponding Author
Prof. Seung Uk Son
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)Search for more papers by this authorNarae Kang
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorDr. Ji Hoon Park
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorKyoung Chul Ko
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorJiseul Chun
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorEunchul Kim
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorDr. Hee-Won Shin
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Search for more papers by this authorDr. Sang Moon Lee
Korea Basic Science Institute, Daejeon 350-333 (Korea)
Search for more papers by this authorDr. Hae Jin Kim
Korea Basic Science Institute, Daejeon 350-333 (Korea)
Search for more papers by this authorCorresponding Author
Prof. Tae Kyu Ahn
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)Search for more papers by this authorCorresponding Author
Prof. Jin Yong Lee
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)Search for more papers by this authorCorresponding Author
Prof. Seung Uk Son
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)
Department of Chemistry and Department of Energy Science Sungkyunkwan University, Suwon 440-746 (Korea)Search for more papers by this authorThis work was supported by grants NRF-2012-045064 (Midcareer Researcher Program) and R31-2008-10029 (WCU program) through NRF of Korea. J.H.P. thanks for grant NRF-2012-1040282 (Priority Research Centers Program). J.Y.L. acknowledges grant NRF-2007-0056343.
Graphical Abstract
Tiny pores: Benzodifuran moieties were introduced into microporous organic networks (MONs) through a tandem process consisting of Sonogashira coupling of 1,3,5-triethynylbenzene and 2,5-diiodo-1,4-hydroquinone and intramolecular cyclization. The resultant benzodifuran-containing MON showed promising photocatalytic activities in the oxidative conversion of primary amines into imines.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
anie_201300655_sm_miscellaneous_information.pdf2.9 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1Recent reviews on MONs:
- 1aJ.-X. Jiang, A. I. Cooper, Top. Curr. Chem. 2010, 293, 1;
- 1bA. Thomas, Angew. Chem. 2010, 122, 8506; Angew. Chem. Int. Ed. 2010, 49, 8328;
- 1cA. I. Cooper, Adv. Mater. 2009, 21, 1291;
- 1dC. Weder, Angew. Chem. 2008, 120, 456; Angew. Chem. Int. Ed. 2008, 47, 448;
- 1eN. B. Mckeown, P. M. Budd, Chem. Soc. Rev. 2006, 35, 675; selected examples
- 1fS. Yuan, S. Kirklin, B. Dorney, D.-J. Liu, L. Yu, Macromolecules 2009, 42, 1554;
- 1gT. 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; Angew. Chem. Int. Ed. 2009, 48, 9457;
- 1hA. Comotti, S. Bracco, M. Mauri, S. Mottadelli, T. Ben, S. Qiu, P. Sozzani, Angew. Chem. 2012, 124, 10283;
10.1002/ange.201205618 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 10136.
- 2
- 2aP. Kaur, J. T. Hupp, S. T. Nguyen, ACS Catal. 2011, 1, 819;
- 2bL. Ma, M. M. Wanderley, W. Lin, ACS Catal. 2011, 1, 691;
- 2cJ. Germain, J. M. J. Fréchet, F. Svec, J. Mater. Chem. 2007, 17, 4989;
- 2dN. B. Mckeown, B. Gahnem, K. J. Msayib, P. M. Budd, C. E. Tattershall, K. Mahmood, S. Tan, D. Book, H. W. Langmi, A. Walton, Angew. Chem. 2006, 118, 1836;
10.1002/ange.200504241 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 1804; Selected examples of photoactive MONs:
- 2eJ. Weber, A. Thomas, J. Am. Chem. Soc. 2008, 130, 6334;
- 2fL. Chen, Y. Honsho, S. Seki, D. Jiang, J. Am. Chem. Soc. 2010, 132, 6742;
- 2gZ. Xie, C. Wang, K. E. deKrafft, W. Lin, J. Am. Chem. Soc. 2011, 133, 2056;
- 2hK. Zhang, D. Kopetzki, P. H. Seeberger, M. Antonietti, F. Vilela, Angew. Chem. 2013, 125, 1472; Angew. Chem. Int. Ed. 2013, 52, 1432.
- 3
- 3aB. Kiskan, J. Weber, ACS Macro Lett. 2012, 1, 37;
- 3bH. A. Patel, C. T. Yayuz, Chem. Commun. 2012, 48, 9989;
- 3cW. Lu, J. P. Sculley, D. Yuan, R. Krishna, Z. Wei, H. C. Zhou, Angew. Chem. 2012, 124, 7598; Angew. Chem. Int. Ed. 2012, 51, 7480;
- 3dK. Thiel, R. Zehbe, J. Roeser, P. Strauch, S. Enthaler, A. Thomas, Polym. Chem. 2013, 4, 1848.
- 4Selected examples:
- 4aJ. Chun, I. G. Jung, H. J. Kim, M. Park, M. S. Lah, S. U. Son, Inorg. Chem. 2009, 48, 6353;
- 4bJ. Chun, H. S. Lee, I. G. Jung, S. W. Lee, H. J. Kim, S. U. Son, Organometallics 2010, 29, 1518;
- 4cJ. Choi, H. Y. Yang, H. J. Kim, S. U. Son, Angew. Chem. 2010, 122, 7884; Angew. Chem. Int. Ed. 2010, 49, 7718;
- 4dM. Mastalerz, H. S. Hauswald, R. Stoll, Chem. Commun. 2012, 48, 130.
- 5
- 5aH. Tsuji, C. Mitsui, L. Ilies, Y. Sato, E. Nakamura, J. Am. Chem. Soc. 2007, 129, 11902;
- 5bH. Li, P. Tang, Y. Zhao, S.-X. Liu, Y. Aeschi, L. Deng, J. Braun, B. Zhao, Y. Liu, S. Tan, W. Meier, S. Decurtins, J. Polym. Sci. Part A 2012, 50, 2935;
- 5cS. Keller, C. Yi, C. Li, S.-X. Liu, C. Blum, G. Frei, O. Sereda, A. Neels, T. Wandlowski, S. Decurtins, Org. Biomol. Chem. 2011, 9, 6410.
- 6
- 6aD. E. Fogg, E. N. Santos, Coord. Chem. Rev. 2004, 248, 2365;
- 6bS. U. Son, K. H. Park, Y. K. Chung, J. Am. Chem. Soc. 2002, 124, 6838.
- 7
- 7aJ.-X. Jiang, F. Su, A. Trewin, C. D. Wood, N. L. Campbell, H. Niu, C. Dickinson, A. Y. Ganin, M. J. Rosseinsky, Y. Z. Khimyak, A. I. Cooper, Angew. Chem. 2007, 119, 8728; Angew. Chem. Int. Ed. 2007, 46, 8574;
- 7bJ.-X. Jiang, A. Laybourn, R. Clowes, Y. Z. Khimyak, J. Bacsa, S. J. Higgins, D. J. Adams, A. I. Cooper, Macromolecules 2010, 43, 7577.
- 8
- 8aH. C. Cho, H. S. Lee, J. Chun, S. M. Lee, H. J. Kim, S. U. Son, Chem. Commun. 2011, 47, 917;
- 8bH. S. Lee, J. Choi, J. Jin, J. Chun, S. M. Lee, H. J. Kim, S. U. Son, Chem. Commun. 2012, 48, 94;
- 8cN. Kang, J. H. Park, J. Choi, J. Jin, J. Chun, I. G. Jung, J. Jeong, J.-G. Park, S. M. Lee, H. J. Kim, S. U. Son, Angew. Chem. 2012, 124, 6730; Angew. Chem. Int. Ed. 2012, 51, 6626;
- 8dJ. Chun, J. H. Park, J. Kim, S. M. Lee, H. J. Kim, S. U. Son, Chem. Mater. 2012, 24, 3458.
- 9S. H. Lim, Y. Su, S. M. Cohen, Angew. Chem. 2012, 124, 5196; Angew. Chem. Int. Ed. 2012, 51, 5106.
- 10J. K. Lee, Y. H. Jung, J. B. H. Tok, Z. Bao, ACS Nano 2011, 5, 2067.
- 11The MONs containing hydroqinone moieties were reported. R. Dawson, A. Laybourn, R. Clowes, Y. Z. Khimyak, D. J. Adams, A. I. Cooper, Macromolecules 2009, 42, 8809.
- 12J. R. Choi, T. Tachikawa, M. Fujitsuka, T. Majima, Langmuir 2010, 26, 10427.
- 13
- 13aJ. H. Park, K. C. Ko, E. Kim, N. Park, J. H. Ko, D. H. Ryu, T. K. Ahn, J. Y. Lee, S. U. Son, Org. Lett. 2012, 14, 5502;
- 13bX. Lang, H. Ji, C. Chen, W. Ma, J. Zhao, Angew. Chem. 2011, 123, 4020; Angew. Chem. Int. Ed. 2011, 50, 3934;
- 13cF. Su, S. C. Mathew, L. Möhlmann, M. Antonietti, X. Wang, S. Blechert, Angew. Chem. 2011, 123, 683; Angew. Chem. Int. Ed. 2011, 50, 657;
- 13dY. Mitsumoto, M. Nitta, J. Org. Chem. 2004, 69, 1256.
- 14G. Jiang, J. Chen, J. S. Huang, C. M. Che, Org. Lett. 2009, 11, 4568.
- 15J. W. Tucker, C. R. Stephenson, J. Org. Chem. 2012, 77, 1617.
- 16M. C. DeRosa, R. J. Crutchley, Coord. Chem. Rev. 2002, 233, 351.
- 17The relevant reaction mechanism was suggested in Ref. [13 b]. However, the possibility of phenylmethanimine generation and the successive addition of amine, and the singlet-oxygen pathway cannot be excluded.