Artigo Revisado por pares

Anthryloligothienylporphyrins: Energy Transfer and Light-Harvesting Systems

1998; Wiley; Volume: 4; Issue: 2 Linguagem: Inglês

10.1002/(sici)1521-3765(19980210)4

ISSN

1521-3765

Autores

Martin S. Vollmer, Frank Würthner, Franz Effenberger, P. Emele, Dirk Meyer, Thomas Stümpfig, H. Port, Hans Christoph Wolf,

Tópico(s)

Photochromic and Fluorescence Chemistry

Resumo

Chemistry – A European JournalVolume 4, Issue 2 p. 260-269 Full Paper Anthryloligothienylporphyrins: Energy Transfer and Light-Harvesting Systems Martin S. Vollmer, Martin S. Vollmer Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code+(49) 711-685-4269Search for more papers by this authorFrank Würthner, Frank Würthner Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code+(49) 711-685-4269Search for more papers by this authorFranz Effenberger, Franz Effenberger [email protected] Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code+(49) 711-685-4269Search for more papers by this authorPeter Emele, Peter Emele 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorDirk U. Meyer, Dirk U. Meyer 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorThomas Stümpfig, Thomas Stümpfig 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorHelmut Port, Helmut Port 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorHans C. Wolf, Hans C. Wolf 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this author Martin S. Vollmer, Martin S. Vollmer Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code+(49) 711-685-4269Search for more papers by this authorFrank Würthner, Frank Würthner Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code+(49) 711-685-4269Search for more papers by this authorFranz Effenberger, Franz Effenberger [email protected] Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code+(49) 711-685-4269Search for more papers by this authorPeter Emele, Peter Emele 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorDirk U. Meyer, Dirk U. Meyer 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorThomas Stümpfig, Thomas Stümpfig 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorHelmut Port, Helmut Port 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this authorHans C. Wolf, Hans C. Wolf 3. Physikalisches Institut, Universität Stuttgart, Pfaffenwaldring 57, D-70550 Stuttgart (Germany)Search for more papers by this author First published: 14 December 1998 https://doi.org/10.1002/(SICI)1521-3765(19980210)4:2 3.0.CO;2-9Citations: 116AboutPDF 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 Abstract In the new trichromophoric supermolecule 1, a quantitative intramolecular energy transfer (>98 %) occurs from the anthracene donor to the emitting porphyrin acceptor through the oligothiophene chain after selective UV excitation of anthracene. Energy-transfer properties and fluorescence quantum yields are independent of the oligothiophene chain length. Attachment of further anthrylquinquethienyl chromophores to the porphyrin ring results in an increase in the intensity of characteristic absorption and fluorescence bands. References 1a N. J. Turro, Modern Molecular Photochemistry, University Science Books, Mill Valley, 1991, pp. 321- 361; 1b S. Speiser, Chem. Rev. 1996, 96, 1953– 1976. 2 V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, New York, 1991, pp. 161– 196. 3a R. Huber, Angew. Chem. 1989, 101, 849– 871. 3 Angew. Chem. Int. Ed. Engl. 1989, 28, 848– 870; 3b J. Deisenhoter, H. Michel, Angew. Chem. 1989, 101, 872– 892. 3 Angew. Chem. Int. Ed. Engl. 1989, 28, 829– 849; 3c G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite-Lawless, M. Z. Papiz, R. J. Cogdell, N. W. Isaacs, Nature 1995, 374, 517– 521; 3d T. Pullerits, V. Sundstrom, Ace. Chem. Res. 1996, 29, 381- 389; 3e R. C. Jennings, R. Bassi, G. Zucchelli, Top. Curr. Chem. 1996, 277, 147– 181. 4a H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929– 947. 4 Angew. Chem. Int. Ed. Engl. 1995, 34, 849– 867; 4b D. Gust, T. A. Moore, A. L. Moore, Ace. Chem. Res. 1993, 26, 198– 205; 4c D. Gust, T. A. Moore, Science 1989, 244, 35– 41; 4d M. R. Wasielewski, Chem. Rev. 1992, 92, 435– 461. 5a A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93– 95. 5 Angew. Chem. Int. Ed. Engl. 1997, 36, 135– 137; 5b A. Osuka, N. Tanabe, S. Kawabata, I. Yamazaki, Y. Nishimura, J. Org. Chem. 1995, 60, 7177– 7185; 5c V. S.-Y Lin, S. G. DiMagno, M. J. Therien, Science 1994, 264, 1105– 1111; 5d D. L. Officer, A. K. Burrell, D. C. W. Reid, Chem. Commun. 1996, 1657– 1658; 5e L. Jaquinod, M. O. Senge, R. K. Pandey, T. P. Forsyth, K. M. Smith, Angew. Chem. 1996, 108, 1982– 1984. 5 Angew. Chem. Int. Ed. Engl. 1996, 35, 1840– 1842; 5f H. A. Staab, T. Carell, Angew. Chem. 1994, 106, 1534– 1536. 5 Angew. Chem. Int. Ed. Engl. 1994, 33, 1466– 1468; 5g A. Harriman, J.-P. Sauvage, Chem. Soc. Rev. 1996, 41– 48. 6a H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810– 812. 6 Angew. Chem. Int. Ed. Engl. 1996, 35, 772– 774; 6b C. A. Hunter, R. K. Hyde, Angew. Chem. 1996, 108, 2064– 2067. 6 Angew. Chem. Int. Ed. Engl. 1996, 35, 1936– 1939; 6c S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196– 1200. 6 Angew. Chem. Int. Ed. Engl. 1995, 34, 1096– 1100; 6d J. L. Sessler, B. Wang, A. Harriman, J. Am. Chem. Soc. 1995, 117, 704– 714. 7a H. C. Wolf, in Molecular Electronics–Science and Technology (Ed.: A. Aviram), AIP, New York, 1992, pp. 237– 241; 7b M. C. Petty, M. R. Bryce, D. Bloor, An Introduction to Molecular Electronics, Edward Arnold, London, 1995, and references therein. 8a J.-M. Lehn, Angew. Chem. 1990, 102, 1347– 1362. 8 Angew. Chem. Int. Ed. Engl. 1990, 29, 1304– 1319; 8b J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995, pp. 89– 138; 8c see ret [2], pp. 355– 394. 9a I. S. Lindsey, New J. Chem. 1991, 15, 153– 180; 9b D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242- 1286. 9 Angew. Chem. Int. Ed. Engl. 1996, 35, 1154– 1196. 10a M. P. O'Neil, M. P. Niemczyk, W A. Svec, D. Gosztola, G. L. Gaines III, M. R. Wasielewski, Science 1992, 257, 63– 65; 10b R. W Wagner, I. S. Lindsey, J. Am. Chem. Soc. 1994, 116, 9759– 9760; 10c R. W Wagner, I S. Lindsey, I Seth, V. Palaniappan, D. F Bocian, J. Am. Chem. Soc. 1996, 118, 3996– 3997; 10d J.-S. Hsiao, B. P. Krueger, R. W Wagner, T. E. Johnson, I K. Delaney, D. C. Mauzerall, G. R. Fleming, I S. Lindsey, D. F Bocian, R. I Donohoe, J. Am. Chem. Soc. 1996, 118, 11181– 11193; 10e F Li, S. Gentemann, W. A. Kalsbeck, J. Seth, J. S. Lindsey, D. Holten, D. F Bocian, J. Mater. Chem. 1997, 7, 1245– 1262. 11a S. Prathapan, T. E. Johnson, I S. Lindsey, J. Am. Chem. Soc. 1993, 115, 7519– 7520; 11b I Seth, V. Palaniappan, T. E. Johnson, S. Prathapan, I S. Lindsey, D. E Bocian, J. Am. Chem. Soc. 1994, 116, 10578– 10592. 12 F Würthner, M. S. Vollmer, F Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090– 8099. 13 I M. Tour, Chem. Rev. 1996, 96, 537– 553. 14a P. Bäuerle, Adv. Mater. 1991, 4, 102– 107; 14b P. Bäuerle, T. Fischer, B. Bidlingmeier, A. Stabel, J. P. Rabe, Angew. Chem. 1995, 107, 335– 339. 14 Angew. Chem. Int. Ed. Engl. 1995, 34, 303– 307. 15a F Gamier, R. Hajlaoui, A. Yassar, P. Srivastava, Science 1994, 265, 1684– 1686; 15b G. Horowitz, E Gamier, A. Yassar, R. Hajlaoui, F. Kouki, Adv. Mater. 1996, 8, 52– 54; 15c F Geiger, M. Stoldt, H. Schweizer, P. Bäuerle, E. Umbach, Adv. Mater. 1993, 5, 922– 925. 16a G M. Tsivgoulis, J.-M. Lehn, Chem. Eur. J. 1996, 2, 1399– 1406; 16b G. M. Tsivgoulis, J.-M. Lehn, Adv. Mater. 1997, 9, 39– 42. 17a E. Effenberger, H. Schlosser, P. Bäuerle, S. Maier, H. Port, H. C. Wolf, Angew. Chem. 1988, 100, 274– 277. 17 Angew. Chem. Int. Ed. Engl. 1988, 27, 281– 284; 17b F. Effenberger, H. C. Wolf, New J. Chem. 1991, 15, 117– 123; 17c N. Holl, H. Port, H. C. Wolf, H. Strobel, F. Effenberger, Chem. Rhys. 1993, 176, 215– 220. 18 H. Müller, I Petersen, R. Strohmaier, B. Gompf, W Eisenmenger, M. S. Vollmer, F. Effenberger, Adv. Mater. 1996, 8, 733– 737. 19 J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney, A. M. Marguerettaz, J. Org. Chem. 1987, 52, 827– 836. 20 J. S. Lindsey, R. W. Wagner, J. Org. Chem. 1989, 54, 828– 836. 21 B. Miehlich, Dissertation, Universität Stuttgart, 1996. 22 M. S. Vollmer, Diplomarbeit, Universität Stuttgart, 1993, unpublished results. 23 Fluorescence quantum yields in n-hexane solutions at 295 K (180 K): anthracene: 30% (55%), 3: 75% (88%), and 4a: 17% (28%). 24 N. Holl, Dissertation, Universität Stuttgart, 1993. 25a G. Dirks, A. L. Moore, T A. Moore, D. Gust, Photochem. Photobiol. 1980, 32, 277– 280; 25b A. L. Moore, G. Dirks, D. Gust, T. A. Moore, Photochem. Photobiol. 1980, 32, 691– 695; 25c D. Gust, T. A. Moore, A. L. Moore, C. Devadoss, P. A. Liddell, R. Hermant, R. A. Nieman, L. J. Demanche, J. M. DeGraziano, I. Gouni, J. Am. Chem. Soc. 1992, 114, 3590– 3603. 26a A. Osuka, H. Yamada, K. Maruyama, Chem. Lett. 1990, 1905– 1908; 26b A. Osuka, H. Yamada, K. Maruyama, N. Malaga, T. Asahi, M. Ohkouchi, T. Okada, I. Yamazaki, Y. Nishimura, J. Am. Chem. Soc. 1993, 115, 9439– 9452. 27a T. Förster, Fluoreszenz Organischer Verbindungen, Vandenhoeck & Ruprecht, Göttingen, 1951/1982, p. 199; 27b T. Förster, Z. Naturforsch. 1949, 4a, 321– 321; 27c T Förster, Disc. Paraday Soc. 1959, 27, 7- 17; 27d S. H. Lin, W Z. Xiao, W Dietz, Phys. Rev. E 1993, 47, 3698– 3706. 28 D. L. Dexter, J. Chem. Phys. 1953, 21, 836– 850. 29a B. Heine, E. Sigmund, H. Port, J. Mol. Electron. 1991, 7, 29– 37; 29b V. L. Ermolaev, A. N. Terenin, Soviet Physics Uspekhi 1960, 3, 423– 426. 30 Molecular Modelling: BIOSYM, Insight II, Discover® 95.0/3.00, CVFF Forcefield. 31a M. E. Michel-Beyerle, M. Bixon, I. Jortner, Chem. Phys. Lett. 1988, 151, 188– 194; 31b A. M. Oliver, D. C. Craig, M. N. Paddon-Row, J. Kroon, J. W. Verhoeven, Chem. Phys. Lett. 1988, 150, 366– 373; 31c R. Hoffmann, A. Imamura, W. J. Hehre, J. Am. Chem. Soc. 1968, 90, 1499– 1509; 31d G. D. Scholes, K. P. Ghiggino, A. M. Oliver, M. N. Paddon-Row, J. Phys. Chem. 1993, 97, 11871– 11876. 32 P. Bäuerle, F Würthner, G. Götz, F Effenberger, Synthesis 1993, 1099– 1103. 33 M. Wiechmann, H. Port, W Frey, F Lärmer, T Elsässer, J. Phys. Chem. 1991, 95, 1918– 1923. 34 S. Ates, A. Yildiz, J. Chem. Soc. Faraday Trans. 1 1983, 79, 2853– 2861. Citing Literature Volume4, Issue210 February 1998Pages 260-269 ReferencesRelatedInformation

Referência(s)
Altmetric
PlumX