Title: Cyclic [5]Paraphenyleneacetylene: Synthesis, Properties, and Formation of a Ring‐in‐Ring Complex Showing a Considerably Large Association Constant and Entropy Effect
Abstract: Angewandte Chemie International EditionVolume 46, Issue 7 p. 1086-1088 Communication Cyclic [5]Paraphenyleneacetylene: Synthesis, Properties, and Formation of a Ring-in-Ring Complex Showing a Considerably Large Association Constant and Entropy Effect† Takeshi Kawase Prof. Dr., Takeshi Kawase Prof. Dr. [email protected] Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorYoshitaka Nishiyama, Yoshitaka Nishiyama Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorTakamitsu Nakamura, Takamitsu Nakamura Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorTakahiro Ebi, Takahiro Ebi Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorKouzou Matsumoto Dr., Kouzou Matsumoto Dr. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorHiroyuki Kurata Dr., Hiroyuki Kurata Dr. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorMasaji Oda Prof. Dr., Masaji Oda Prof. Dr. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this author Takeshi Kawase Prof. Dr., Takeshi Kawase Prof. Dr. [email protected] Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorYoshitaka Nishiyama, Yoshitaka Nishiyama Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorTakamitsu Nakamura, Takamitsu Nakamura Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorTakahiro Ebi, Takahiro Ebi Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorKouzou Matsumoto Dr., Kouzou Matsumoto Dr. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorHiroyuki Kurata Dr., Hiroyuki Kurata Dr. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this authorMasaji Oda Prof. Dr., Masaji Oda Prof. Dr. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Fax: (+81) 6-6850-5387Search for more papers by this author First published: 29 January 2007 https://doi.org/10.1002/anie.200603707Citations: 59 † This work was supported by Grant-in-Aids for Scientific Research (B) (No. 16350073) and Exploratory Research (18655016) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation 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 In the ring: The title compound ([5]CPPA), the smallest belt-shaped conjugated system known to date, forms a considerably stable ring-in-ring complex with [8]CPPA (see picture). [8]CPPA⊃[5]CPPA has a smaller contact area than [9]CPPA⊃[6]CPPA but its large Ka and ΔH values reveal that the interaction results from the electrostatic attractive force rather than the dispersion force. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z603707_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. Kroto, K. G. Mckay, Nature 1988, 331, 328–331; 10.1038/331328a0 CASWeb of Science®Google Scholar 1bS. Iijima, J. Cryst. Growth 1989, 50, 675–683; 10.1016/0022-0248(80)90013-5 Web of Science®Google Scholar 1cD. Ugarte, Nature 1992, 359, 707–709. 10.1038/359707a0 CASPubMedWeb of Science®Google Scholar 2 2aS. Iijima, Nature 1991, 354, 56–58; 10.1038/354056a0 CASWeb of Science®Google Scholar 2bB. W. Smith, M. Monthioux, D. E. Luzzi, Nature 1998 396, 323–325. 10.1038/24521 CASWeb of Science®Google Scholar 3 3aB. W. Smith, M. Monthioux, D. E. Luzzi, Nature 1998, 396, 323–324; 10.1038/24521 CASWeb of Science®Google Scholar 3bJ. Sloan, A. I. Kirkland, J. L. Hutchison, M. L. H. Green, Chem. Commun. 2002, 1319–1332. 10.1039/b200537a CASWeb of Science®Google Scholar 4 4aR. C. Haddon, Science 1993, 261, 1545–1550; 10.1126/science.261.5128.1545 CASPubMedWeb of Science®Google Scholar 4bM. Kamieth, F.-G. Klärner, F. Diederich, Angew. Chem. 1998, 110, 3497–3500; 10.1002/(SICI)1521-3757(19981204)110:23<3497::AID-ANGE3497>3.0.CO;2-G Google ScholarAngew. Chem. Int. Ed. 1998, 37, 3303–3306; 10.1002/(SICI)1521-3773(19981217)37:23<3303::AID-ANIE3303>3.0.CO;2-T CASPubMedWeb of Science®Google Scholar 4cL. T. Scott, Pure Appl. Chem. 1999, 71, 209–219; 10.1351/pac199971020209 CASWeb of Science®Google Scholar 4dK. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 5332–5333; 10.1021/ja983744+ CASWeb of Science®Google Scholar 4eR. B. Ansems, L. T. Scott, J. Phys. Org. Chem. 2004, 17, 819–823; 10.1002/poc.800 CASWeb of Science®Google Scholar 4fU. D. Priyakumar, M. Punnagai, G. P. Krishna Mohan, G. N. Sastry, Tetrahedron 2004, 60, 3037–3043; 10.1016/j.tet.2004.01.086 CASWeb of Science®Google Scholar 4gY.-T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870–6884. 10.1021/ja058391a CASPubMedWeb of Science®Google Scholar 5 5aR. Saito, G. Dresselhaus, M. S. Dresselhaus, J. Appl. Phys. 1993, 73( 2), 494–500; 10.1063/1.353358 Web of Science®Google Scholar 5bJ. Cumings, A. Zettl, Science 2000, 289, 602–604; 10.1126/science.289.5479.602 CASPubMedWeb of Science®Google Scholar 5cA. N. Khlobystov, D. A. Britz, G. A. D. Briggs, Acc. Chem. Res. 2005, 38, 901–909. 10.1021/ar040287v CASPubMedWeb of Science®Google Scholar 6J. Lu, S. Nagase, X. Zhang, D. Wang, M. Ni, Y. Maeda, T. Wakahara, T. Nakahodo, T. Tsuchiya, T. Akasaka, Z. Gao, D. Yu, H. Ye, W. N. Mei, Y. Zhou, J. Am. Chem. Soc. 2006, 128, 5114–5118, and references therein. 10.1021/ja058214+ CASPubMedWeb of Science®Google Scholar 7 7aT. Kawase, H. R. Darabi, M. Oda, Angew. Chem. 1996, 108, 2803–2805; 10.1002/ange.19961082214 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 2662–2664; 10.1002/anie.199626621 CASWeb of Science®Google Scholar 7bT. Kawase, N. Ueda, K. Tanaka, Y. Seirai, M. Oda, Tetrahedron Lett. 2001, 42, 5509–5511; 10.1016/S0040-4039(01)00862-0 CASWeb of Science®Google Scholar 7cT. Kawase, M. Oda, Pure Appl. Chem. 2006, 77, 831–839. 10.1351/pac200678040831 CASWeb of Science®Google Scholar 8T. Kawase, H. R. Darabi, K. Tanaka, M. Oda, Angew. Chem. 2003, 115, 1662–1666; 10.1002/ange.200250728 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 1624–1628. 10.1002/anie.200250728 CASPubMedWeb of Science®Google Scholar 9T. Kawase, K. Tanaka, N. Shiono, Y. Seirai, M. Oda, Angew. Chem. 2004, 116, 1754–1756; 10.1002/ange.200353517 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 1722–1724. 10.1002/anie.200353517 CASPubMedWeb of Science®Google Scholar 10Ring-in-ring complexes; Google Scholar 10aS. Kamitori, K. Hirotsu, T. Higuchi, J. Am. Chem. Soc. 1987, 109, 2409–2414; 10.1021/ja00242a026 CASWeb of Science®Google Scholar 10bS.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 2177–2179; 10.1002/1521-3757(20010601)113:11<2177::AID-ANGE2177>3.0.CO;2-G Google ScholarAngew. Chem. Int. Ed. 2001, 40, 2119–2121; 10.1002/1521-3773(20010601)40:11<2119::AID-ANIE2119>3.0.CO;2-4 CASPubMedWeb of Science®Google Scholar 10cS.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. Williams, Angew. Chem. 2002, 114, 280–284; 10.1002/1521-3757(20020118)114:2<280::AID-ANGE280>3.0.CO;2-Q Google ScholarAngew. Chem. Int. Ed. 2002, 41, 270–274; 10.1002/1521-3773(20020118)41:2<270::AID-ANIE270>3.0.CO;2-5 PubMedWeb of Science®Google Scholar 10dA. I. Day, R. J. Blanch, R. J. Arnold, G. R. Lewis, I. Dance, Angew. Chem. 2002, 114, 285–287; 10.1002/1521-3757(20020118)114:2<285::AID-ANGE285>3.0.CO;2-6 Web of Science®Google ScholarAngew. Chem. Int. Ed. 2002, 41, 275–277; 10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M CASPubMedWeb of Science®Google Scholar 10eJ. C. Loren, M. Yoshizawa, R. F. Haldimann, A. Linden, J. S. Siegel, Angew. Chem. 2003, 115, 5880–5883; 10.1002/ange.200352562 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 5702–5705; 10.1002/anie.200352562 CASPubMedWeb of Science®Google Scholar 10fS. J. Dalgarno, J. Fisher, C. L. Raston, Chem. Eur. J. 2006, 12, 2772–2777; 10.1002/chem.200500968 CASPubMedWeb of Science®Google Scholar 10gT. Iwanaga, R. Nakamoto, M. Yasutake, H. Takemura, K. Sako, T. Shinmyozu, Angew. Chem. 2006, 118, 3725–3729; 10.1002/ange.200504499 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 3643–3647. 10.1002/anie.200504499 CASPubMedWeb of Science®Google Scholar 11Procedures for the synthesis and physical properties of new compounds are shown in the Supporting Information. Google Scholar 12I. Tabushi, H. Yamada, Y. Kuroda, J. Org. Chem. 1975, 40, 1946–1949. 10.1021/jo00901a016 CASWeb of Science®Google Scholar 13Because of the susceptibility of 1 to oxygen, it is difficult to measure a small quantity of 1 accurately. Thus, the quantity of 1 in chloroform was determined from an NMR spectrum by using adamantane as a standard. The solution in chloroform was diluted about 20-fold with cyclohexane, and the absorption and emission spectra were recorded. Google Scholar 14 14aJ. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445–1449; 10.1002/ange.19941061322 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1994, 33, 1360–1363; 10.1002/anie.199413601 Web of Science®Google Scholar 14bJ. M. Tour, Chem. Rev. 1996, 96, 537–553. 10.1021/cr9500287 CASPubMedWeb of Science®Google Scholar 15K. Hirose, J. Inclusion Phenom. Macrocyclic Chem. 2001, 39, 193–209. 10.1023/A:1011117412693 CASWeb of Science®Google Scholar 16 16aM. Yanase, M. Matsuoka, Y. Tatsumi, M. Suzuki, H. Iwamoto, T. Haino, Y. Fukazawa, Y. Tetrahedron Lett. 2000, 41, 493–497; 10.1016/S0040-4039(99)02099-7 CASWeb of Science®Google Scholar 16bK. Tashiro, Y. Hirabayashi, T. Aida, K. Saigo, K. Fujiwara, K. Komatsu, S. Sakamoto, K. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 12086–12087; 10.1021/ja0264450 CASPubMedWeb of Science®Google Scholar 16cT. Haino, M. Yanase, C. Fukunaga, Y. Fukazawa, Tetrahedron 2006, 62, 2025–2035; 10.1016/j.tet.2005.07.121 CASWeb of Science®Google Scholar 16dP. E. Georghiou, A. H. Tran, S. S. Stroud, D. W. Thompson, Tetrahedron 2006, 62, 2036–2044. 10.1016/j.tet.2005.09.151 CASWeb of Science®Google Scholar 17 17aF. Diederich, M. Gomez-Lopez, Chem. Soc. Rev. 1999, 28, 263–277; 10.1039/a804248i CASWeb of Science®Google Scholar 17bM. J. Hardie, C. L. Raston, Chem. Commun. 1999, 1153–1163; 10.1039/a900787c CASWeb of Science®Google Scholar 17cP. D. W. Boyd, C. A. Reed, Acc. Chem. Res. 2005, 38, 235–242. 10.1021/ar040168f CASPubMedWeb of Science®Google Scholar 18T. Kawase, H. Kurata, Chem. Rev., 2006, 106, 5250–5273. 10.1021/cr0509657 CASPubMedWeb of Science®Google Scholar 19 19aH.-B. Bürgi, E. Blanc, D. Schwarzenbach, S. Lui, Y.-j. Lu, M. M. Kappes, J. A. Ibers, Angew. Chem. 1992, 104, 667–670; 10.1002/ange.19921040544 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1992, 31, 640–643; 10.1002/anie.199206401 Web of Science®Google Scholar 19bA. L. Balch, V. J. Catalano, J. W. Lee, M. M. Olmstead, J. Am. Chem. Soc. 1992, 114, 5455–5456; 10.1021/ja00039a084 CASWeb of Science®Google Scholar 19cY. Umezawa, M. Nishio, CrystEngComm 2003, 5, 514–518, and references therein. 10.1039/b311953j CASWeb of Science®Google Scholar 20 20aJ. S. Moore, Acc. Chem. Res. 1997, 30, 402–413; 10.1021/ar950232g CASWeb of Science®Google Scholar 20bY. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Adachi, S. Araki, M. Sonoda, K. Hirose, K. Naemura, J. Am. Chem. Soc. 2002, 124, 5350–5364; 10.1021/ja012458m CASPubMedWeb of Science®Google Scholar 20cD. Zhao, J. S. Moore, Chem. Commun. 2003, 807–818; 10.1039/b207442g CASPubMedWeb of Science®Google Scholar 20dS. Höger, Chem. Eur. J. 2004, 10, 1320–1329. 10.1002/chem.200305496 CASPubMedWeb of Science®Google Scholar 21 21aC. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525–5534; 10.1021/ja00170a016 CASWeb of Science®Google Scholar 21bC. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651–669; 10.1039/b008495f CASWeb of Science®Google Scholar 21cE. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244–1287; 10.1002/ange.200390290 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 1210–1250. 10.1002/anie.200390319 CASPubMedWeb of Science®Google Scholar 22The first theoretical study on carbon nanorings: I. Garcia Cuesta, T. B. Pedersen, H. Hoch, A. Sanchez de Meras, ChemPhysChem, 2006, 7, 2503–2507. 10.1002/cphc.200600362 CASPubMedWeb of Science®Google Scholar Citing Literature Volume46, Issue7February 5, 2007Pages 1086-1088 ReferencesRelatedInformation
Publication Year: 2006
Publication Date: 2006-12-20
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
Access and Citation
Cited By Count: 64
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot