Voltar
Artigo Acesso aberto Revisado por pares
BIBTEX RIS

Rotaxane Building Blocks bearing Blocked Isocyanate Stoppers: Polyrotaxanes through Post‐Assembly Chain Extension

2003; Wiley; Volume: 115; Issue: 29 Linguagem: Inglês

10.1002/ange.200351458

ISSN

1521-3757

Autores

Timothy J. Kidd, Ton Loontjens, David A. Leigh, Jenny K. Y. Wong,

Tópico(s)

Advanced Polymer Synthesis and Characterization

Resumo

Angewandte ChemieVolume 115, Issue 29 p. 3501-3505 Zuschrift Rotaxane Building Blocks bearing Blocked Isocyanate Stoppers: Polyrotaxanes through Post-Assembly Chain Extension† Timothy J. Kidd Dr., Timothy J. Kidd Dr. DSM Research, P.O. Box 18, 6160 MD Geleen, The Netherlands, Fax: (+31) 46-476-3949Search for more papers by this authorTon J. A. Loontjens Dr., Ton J. A. Loontjens Dr. [email protected] DSM Research, P.O. Box 18, 6160 MD Geleen, The Netherlands, Fax: (+31) 46-476-3949Search for more papers by this authorDavid A. Leigh Prof. Dr., David A. Leigh Prof. Dr. [email protected] School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK, Fax: (+44) 131-667-9085Search for more papers by this authorJenny K. Y. Wong Dr., Jenny K. Y. Wong Dr. School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK, Fax: (+44) 131-667-9085Search for more papers by this author Timothy J. Kidd Dr., Timothy J. Kidd Dr. DSM Research, P.O. Box 18, 6160 MD Geleen, The Netherlands, Fax: (+31) 46-476-3949Search for more papers by this authorTon J. A. Loontjens Dr., Ton J. A. Loontjens Dr. [email protected] DSM Research, P.O. Box 18, 6160 MD Geleen, The Netherlands, Fax: (+31) 46-476-3949Search for more papers by this authorDavid A. Leigh Prof. Dr., David A. Leigh Prof. Dr. [email protected] School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK, Fax: (+44) 131-667-9085Search for more papers by this authorJenny K. Y. Wong Dr., Jenny K. Y. Wong Dr. School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK, Fax: (+44) 131-667-9085Search for more papers by this author First published: 24 July 2003 https://doi.org/10.1002/ange.200351458Citations: 14 † This work was carried out as part of the European Training and Mobility of Researchers (TMR) European Network the Development of Rotaxane-based Unconventional Materials (contract no. ERBFMRXCT970097). D.A.L. is an EPSRC Advanced Research Fellow (AF/982324). Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Ein einfacher und vielseitiger Zugang zu Polyrotaxanen mit vielfältigen Topologien besteht in der Synthese und anschließenden Polymerisation stabiler Rotaxan-Monomere mit sterisch anspruchsvollen Isocyanat-Gruppen als Stoppergruppen (siehe Schema). Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2003/z51458_s.pdf or from the author. 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 1 1aH. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843–945; 10.1016/0079-6700(94)90034-5 CASWeb of Science®Google Scholar 1bH. W. Gibson in Large Ring Molecules (Ed.: ), Wiley, New York, 1996, pp. 191–262; Google Scholar 1cA. Harada, Acta Polym. 1998, 49, 3–17; 10.1002/(SICI)1521-4044(199801)49:1 3.0.CO;2-G CASWeb of Science®Google Scholar 1dH. W. Gibson, C. Gong in Molecular Catenanes, Rotaxanes and Knots (Ed ), VCH, Weinheim, 1999, pp. 277–321; 10.1002/9783527613724.ch11 Web of Science®Google Scholar 1eF. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643–1663. 10.1021/cr970081q CASPubMedWeb of Science®Google Scholar 2 2aR. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133–137; 10.1038/369133a0 CASWeb of Science®Google Scholar 2bM.-V. Martinez-Diaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991–1994; 10.1002/ange.19971091735 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 1904–1907; 10.1002/anie.199719041 CASWeb of Science®Google Scholar 2cL. Raehm, J.-M. Kern, J.-P. Sauvage, Chem. Eur. J. 1999, 5, 3310–3317; 10.1002/(SICI)1521-3765(19991105)5:11 3.0.CO;2-R CASWeb of Science®Google Scholar 2dW. Clegg, C. Gimenez-Saiz, D. A. Leigh, A. Murphy, A. M. Z. Slawin, S. J. Teat, J. Am. Chem. Soc. 1999, 121, 4124–4129; 10.1021/ja9841310 CASWeb of Science®Google Scholar 2eA. M. Brouwer, C. Frochot, F. G. Gatti, D. A. Leigh, L. Mottier, F. Paolucci, S. Roffia, G. W. H. Wurpel, Science 2001, 291, 2124–2128; 10.1126/science.1057886 CASPubMedWeb of Science®Google Scholar 2fM. C. Jimenez-Molero, C. Dietrich-Buchecker, J.-P. Sauvage, Chem. Eur. J. 2002, 8, 1456–1466; 10.1002/1521-3765(20020315)8:6 3.0.CO;2-H CASPubMedWeb of Science®Google Scholar 2gY. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H. R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, ChemPhysChem 2002, 3, 519–525; 10.1002/1439-7641(20020617)3:6 3.0.CO;2-2 CASPubMedWeb of Science®Google Scholar 2hC. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2002, 114, 1847–1850; 10.1002/1521-3757(20020517)114:10 3.0.CO;2-Z Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1769–1772; For recent accounts from the UCLA and Strasbourg groups, see: 10.1002/1521-3773(20020517)41:10 3.0.CO;2-N PubMedWeb of Science®Google Scholar 2iA. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Res. 2001, 34, 433–444; 10.1021/ar000178q CASPubMedWeb of Science®Google Scholar 2jJ. P. Collin, C. Dietrich-Buchecker, P. Gavina, M. C. Jimenez-Molero, J.-P. Sauvage, Acc. Chem. Res. 2001, 34, 477–487. 10.1021/ar0001766 CASPubMedWeb of Science®Google Scholar 3 3aV. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484–3530; 10.1002/1521-3757(20001002)112:19 3.0.CO;2-O Google ScholarAngew. Chem. Int. Ed. 2000, 39, 3349–3391; Google Scholar 3bSpecial issue on Molecular Machines, Acc. Chem. Res. 2001, 34, 409–522; Web of Science®Google Scholar 3c“Molecular Machines and Motors”: Struct. Bonding (Berlin) Vol. 99, 2001. Google Scholar 4D. A. Wicks, Z. W. Wicks, Jr., Prog. Org. Coat. 1999, 36, 148–172, and references therein. 10.1016/S0300-9440(99)00042-9 CASWeb of Science®Google Scholar 5For other examples of post-assembly elaboration of rotaxanes, see: Google Scholar 5aM. P. L. Werts, M. van der Boogaard, G. Hadziioannou, G. M. Tsivgoulis, Chem. Commun. 1999, 623–624; 10.1039/a900914k CASWeb of Science®Google Scholar 5bS. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Org. Lett. 2000, 2, 759–762; 10.1021/ol9913587 CASPubMedWeb of Science®Google Scholar 5cS. J. Rowan, J. F. Stoddart, J. Am. Chem. Soc. 2000, 122, 164–165; 10.1021/ja992919s CASWeb of Science®Google Scholar 5dD. W. Zehnder, D. B. Smithrud, Org. Lett. 2001, 3, 2485–2487; 10.1021/ol016107o CASPubMedWeb of Science®Google Scholar 5eS.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170–5183; 10.1002/1521-3765(20021115)8:22 3.0.CO;2-S CASPubMedWeb of Science®Google Scholar 5fS.-H. Chiu, S. J. Rowan, S. J. Cantrill, L. Ridvan, P. R. Ashton, R. L. Garrell, J. F. Stoddart, Tetrahedron 2002, 58, 807–814. 10.1016/S0040-4020(01)01110-3 CASWeb of Science®Google Scholar 6Other approaches for controlling the macrocycle:thread repeat-unit stoichiometry in polyrotaxanes include Google Scholar 6athe polymerization of monomer threads containing bulky blocking groups [I. Yamaguchi, K. Osakada, T. Yamamoto, J. Am. Chem. Soc. 1996, 118, 1811–1812; 10.1021/ja953101j CASWeb of Science®Google ScholarC. Gong, T. E. Glass, H. W. Gibson, Macromolecules 1998, 31, 308–313; 10.1021/ma970812o CASWeb of Science®Google ScholarC. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426–2428; 10.1002/ange.19971092111 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 2331–2333; 10.1002/anie.199723311 CASWeb of Science®Google ScholarM. B. Steinbrunn, G. Wenz, Angew. Chem. 1996, 108, 2274–2277; 10.1002/ange.19961081827 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 2139–2141] and/or initiators [ 10.1002/anie.199621391 CASWeb of Science®Google ScholarH. W. Gibson, P. T. Engen, S. H. Lee, Polymer 1999, 40, 1823–1832] in the presence of a macrocycle; 10.1016/S0032-3861(98)00392-9 CASWeb of Science®Google Scholar 6bthe formation of a pseudorotaxane coordination polymer [D. Whang, Y.-M. Yeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11 333–11 334; 10.1021/ja961551l CASWeb of Science®Google ScholarD. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451–452; 10.1021/ja963096z CASWeb of Science®Google ScholarE. Lee, J. Heo, K. Kim, Angew. Chem. 2000, 112, 2814–2819; 10.1002/1521-3757(20000804)112:15 3.0.CO;2-S Web of Science®Google ScholarAngew. Chem. Int. Ed. 2000, 39, 2699–2701]; and 10.1002/1521-3773(20000804)39:15 3.0.CO;2-Z CASPubMedWeb of Science®Google Scholar 6cthe catalytic polymerization of monomer threads where the threaded macrocycle itself acts as the catalyst to polymer formation [D. Tuncel, J. H. G. Steinke, Chem. Commun. 1999, 1509–1510]. 10.1039/a902990g CASWeb of Science®Google Scholar 7J. A. Loontjens, B. J. M. Plum (DSM), WO patent 00/17169, 2000. Google Scholar 8 8aF. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983–5989; 10.1021/ja001697r CASPubMedWeb of Science®Google Scholar 8bF. G. Gatti, S. Leòn, J. K. Y. Wong, G. Bottari, A. Altieri, M. A. Farran Morales, S. J. Teat, C. Frochot, D. A. Leigh, A. M. Brouwer, F. Zerbetto, Proc. Natl. Acad. Sci. USA 2003, 100, 10–14. 10.1073/pnas.0134757100 CASPubMedWeb of Science®Google Scholar 9Full details of the experimental procedures can be found in the Supporting Information. Google Scholar 10Detailed crystallographic data for these compounds is reported in the Supporting Information. Google Scholar 11A rotaxane similar to 5 but without the extra phenylalanine residues (Figure 1 c) was synthesized through condensation of two equivalents of stopper 1 with fumaroyl chloride. Subsequent polymerization of this rotaxane monomer resulted in the dethreading of the macrocycle from the polymer as a result of the loss of the bulky caprolactam blocking group during chain extension. Google Scholar 12The calculated degree of polymerization was based on the SEC-determined average molecular weights of Jeffamine D400 and rotaxane monomers. Google Scholar Citing Literature Volume115, Issue29July 28, 2003Pages 3501-3505 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation

Referência(s)