Thermal and Photochemical Properties of 4′,7-Dihydroxyflavylium in Water–Ionic Liquid Biphasic Systems: A Write–Read–Erase Molecular Switch†
Fernando Pina Prof.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorJoão C. Lima Dr.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorA. Jorge Parola Dr.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorCarlos A. M. Afonso Dr.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorFernando Pina Prof.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorJoão C. Lima Dr.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorA. Jorge Parola Dr.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorCarlos A. M. Afonso Dr.
REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal, Fax: (+351) 21-294-8550
Search for more papers by this authorWe thank the Fundação para a Ciência e Tecnologia and FEDER for projects POCTI/QUI/47357/2002 and POCTI/EQU/35437/1999.
Graphical Abstract
Auf Gelb geschaltet: 4′,7-Dihydroxyflavylium (AH+) in Zweiphasensystemen Wasser/ionische Flüssigkeit kann als Schreib-Lese-Lösch-System verwendet werden. Im Sauren ist die Chalcon-Form (Ct) in ionischen Flüssigkeiten löslich und thermisch metastabil, reagiert aber photochemisch (Schreibprozess) unter Bildung eines gelben Flavyliumsalzes, das optisch ausgelesen werden kann, ohne dabei gelöscht zu werden. Das System wird durch zwei pH-Sprünge für einen neuen Zyklus regeneriert.
Supporting Information
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References
- 1
- 1aF. Pina, M. Maestri, V. Balzani, Handbook of Photochemistry and Photobiology, Vol. 3, American Scientific Publication, Research Triangle Park, 2003, chap. 9, pp. 411– 449;
- 1bF. Pina, M. J. Melo, M. Maestri, R. Ballardini, V. Balzani, J. Am. Chem. Soc. 1997, 119, 5556–5561;
- 1cF. Pina, A. Roque, M. J. Melo, M. Maestri, L. Belladelli, V. Balzani, Chem. Eur. J. 1998, 4, 1184–1191;
10.1002/(SICI)1521-3765(19980710)4:7<1184::AID-CHEM1184>3.0.CO;2-6 CAS Web of Science® Google Scholar
- 1dF. Pina, M. J. Melo, M. Maestri, P. Passaniti, V. Balzani, J. Am. Chem. Soc. 2000, 122, 4496–4498;
- 1eA. Roque, C. Lodeiro, F. Pina, M. Maestri, S. Dumas, P. Passaniti, V. Balzani, J. Am. Chem. Soc. 2003, 125, 987–994.
- 2
- 2aS. V. Dzyuba, R. A. Bartsch, Angew. Chem. 2003, 115, 158–160;
10.1002/ange.200390038 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 148–150;
- 2bK. R. Seddon, Nat. Mater. 2003, 2, 1;
- 2cJ. H. Davis Jr., P. A. Fox, Chem. Commun. 2003, 1209–1212;
- 2dH. Zhao, S. V. Malhotra, Aldrichimica Acta 2002, 35, 75–83;
- 2eJ. F. Brennecke, E. J. Maginn, AIChE J. 2001, 47, 2384–2389;
- 2fJ. Dupont, C. S. Consorti, J. Spencer, J. Braz. Chem. Soc. 2000, 11, 337–344;
- 2gP. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926–3945;
10.1002/1521-3757(20001103)112:21<3926::AID-ANGE3926>3.0.CO;2-U Google ScholarAngew. Chem. Int. Ed. 2000, 39, 3772–3789;10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
- 2hT. Welton, Chem. Rev. 1999, 99, 2071–2083.
- 3
- 3aJ. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667–3692;
- 3bR. Sheldon, Chem. Commun. 2001, 2399–2407;
- 3cC. M. Gordon, Appl. Catal. A 2001, 222, 101–117.
- 4
- 4aJ. D. Holbrey, A. E. Visser, S. K. Spear, W. M. Reichert, R. P. Swatloski, G. A. Broker, R. D. Rogers, Green. Chem. 2003, 5, 129–135;
- 4bE. D. Bates, R. D. Mayton, I. Ntai, J. H. Davis, Jr., J. Am. Chem. Soc. 2002, 124, 926–927;
- 4cL. C. Branco, J. G. Crespo, C. A. M. Afonso, Angew. Chem. 2002, 41, 2895–2897;
Angew. Chem. Int. Ed. 2002, 41, 2771–2773;
10.1002/1521-3773(20020802)41:15<2771::AID-ANIE2771>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 4dL. C. Branco, J. G. Crespo, C. A. M. Afonso, Chem. Eur. J. 2002, 8, 3865–3871;
10.1002/1521-3765(20020902)8:17<3865::AID-CHEM3865>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 4eT. Schäfer, C. M. Rodrigues, C. A. M. Afonso, J. G. Crespo, Chem. Commun. 2001, 1622–1623;
- 4fA. G. Fadeev, M. M. Meagher, Chem. Commun. 2001, 295–296.
- 5F. Pina, L. Benedito, M. J. Melo, A. J. Parola, J. C. Lima, A. L. Maçanita, An. Quim. Int. Ed. 1977, 93, 111–118.
- 6M. Maestri, R. Ballardini, F. Pina, M. J. Melo, J. Chem. Educ. 1997, 74, 1314–1316.
- 7F. Pina, M. J. Melo, R. Ballardini, L. Flamigni, M. Maestri, New J. Chem. 1997, 21, 969–976.
- 8
- 8aJ.-F. Huang, P.-Y. Chen, I.-W. Sun, S. P. Wang, Inorg. Chim. Acta 2001, 320, 7–11;
- 8bJ. Dupont, P. A. Z. Suarez, R. F. De Souza, R. A. Burrow, J.-P. Kintzinger, Chem. Eur. J. 2000, 6, 2377–2381;
10.1002/1521-3765(20000703)6:13<2377::AID-CHEM2377>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 8cP. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzel, Inorg. Chem. 1996, 35, 1168–1178;
- 8dJ. Fuller, R. T. Carlin, H. C. De Long, D. Haworth, J. Chem. Soc. Chem. Commun. 1994, 299–300.
- 9J. L. Anderson, J. Ding, T. Welton, D. W. Armstrong, J. Am. Chem. Soc. 2002, 124, 14 247–14 254.
- 10Compare with Figure 3S in the Supporting Information.
- 11An identical cycle was performed with [bmim][NTf2] (Tf=trifluoromethanesulfonyl). In this case, the ionic-liquid phase is more turbid, thus making spectrophotometric measurements difficult.
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