Abstract
Electronic excitation energy transfer along a molecular wire depends on the relative orientation of the electronic transition dipole moments of neighboring chromophores. In porphycenes, this orientation is changed upon double proton transfer in the electronic ground state. We explore the possibility to trigger such a double proton transfer reaction by means of an infrared pump-dump laser control scheme. To this end, a quantum chemical characterization of an asymmetrically substituted porphycene is performed using density functional theory. Ground state geometries, the topology of the potential energy surface for double proton transfer, and \(\hbox{S}_0\rightarrow\hbox{S}_1\) transition energies are compared with the parent compound porphycene and a symmetric derivative. Employing a simple two-dimensional model for the double proton transfer, which incorporates sequential and concerted motions, quantum dynamics simulations of the laser-driven dynamics are performed which demonstrate tautomerization control. Based on the orientation of the transition dipole moments, this tautomerization may lead to an estimated change in the Förster transfer coupling of about 60%.
Similar content being viewed by others
References
Balzani V, Credi A, Venturi M (2003) Molecular devices and machines. Wiley-VCH, Weinheim
Wagner RW, Lindsey JS (1994) J Am Chem Soc 116:9759
Wagner R, Johnson T, Lindsey J (1996) J Am Chem Soc 118:11166
Hsiao J, Krueger B, Wagner R, Johnson T, Delaney J, Mauzerall D, Fleming G, Lindsey J, Bocian D, Donohoe R (1996) J Am Chem Soc 118:11181
Seth J, Palaniappan V, Wagner R, Johnson T, Lindsey J, Bocian D (1996) J Am Chem Soc 118:11194
Li J, Ambroise A, Yang S, Diers J, Seth J, Wack C, Bocian D, Holten D, Lindsey J (1999) J Am Chem Soc 121:8927
Ambroise A, Wagner R, Rao P, Riggs J, Hascoat P, Diers J, Seth J, Lammi R, Bocian D, Holten D, Lindsey J (2001) Chem Mater 13:1023
Lammi R, Wagner R, Ambroise A, Diers J, Bocian D, Holten D, Lindsey J (2001) J Phys Chem B 105:5341
Holten D, Bocian D, Lindsey J (2002) Acc Chem Res 35:57
Song H, Taniguchi M, Diers JR, Kirmaier C, Bocian DF, Lindsey JS, Holten D (2009) J Phys Chem B 113:16483
Heilemann M, Tinnefeld P, Mosteiro G, Garcia-Parajo M, Hulst NV, Sauer M (2004) J Am Chem Soc 126:6514
Tinnefeld P, Heilemann M, Sauer M (2005) Chem Phys Chem 6:217
Sanchez-Mosteiro G, van Dijk EMHP, Hernando J, Heilemann M, Tinnefeld P, Sauer M, Koberlin F, Patting M, Wahl M, Erdmann R, van Hulst NF, Garcia-Parajo MF (2006) J Phys Chem B 110:26349
Heilemann M, Kasper R, Tinnefeld P, Sauer M (2006) J Am Chem Soc 128:16864
Vyawahare S, Eyal S, Mathews K, Quake S (2004) Nano Lett 4:1035
Bahr J, Kodis G, de la Garza L, Lin S, Moore A, Moore T, Gust D (2001) J Am Chem Soc 123:7124
Wagner R, Lindsey J, Seth J, Palaniappan V, Bocian D (1996) J Am Chem Soc 118:3996
Akasaka T, Otsuki J, Araki K (2002) Chem Eur J 8:130
Albelda M, Diaz P, Garcia-Espana E, Lima J, Lodeiro C, de Melo J, Parola A, Pina F, Soriano C (2002) Chem Phys Lett 353:63
Otsuki J, Akasaka T, Araki K (2008) Coord Chem Rev 252:32
Straight SD, Liddell PA, Terazono Y, Moore TA, Moore AL, Gust D (2007) Adv Funct Mater 17:777
Abdel-Latif MK, Kühn O (2010) Chem Phys 368:76
May V, Kühn O (2011) Charge and energy transfer dynamics in molecular systems, 3rd revised and enlarged edition. Wiley-VCH, Weinheim
Waluk J (2007) In: Hynes J, Klinman J, Limbach H-H, Schowen R (eds) Hydrogen transfer reactions. VCH-Wiley, Weinheim, p 245
Gil M, Jasny J, Vogel E, Waluk J (2000) Chem Phys Lett 323:534
Frisch MJ et al (2004) Gaussian 03, Revision C.02. Gaussian Inc, Wallingford
Meyer H-D, Manthe U, Cederbaum LS (1990) Chem Phys Lett 165:73
Beck MH, Jäckle A, Worth GA, Meyer H-D (2000) Phys Rep 324:1
Worth G, Beck M, Jäckle A, Meyer H-D (2007) The MCTDH package, Version 8.4. University of Heidelberg, Heidelberg
Meyer H-D, Quere FL, Leonard C, Gatti F (2006) Chem Phys 329:179
Smedarchina Z, Shibl MF, Kühn O, Fernández-Ramos A (2007) Chem Phys Lett 436:314
Shibl MF, Pietrzak M, Limbach H-H, Kühn O (2007) Chem Phys Chem 8:315
Smedarchina Z, Siebrand W, Fernandez-Ramos A (2007) J Chem Phys 127:174513
Smedarchina Z, Siebrand W, Fernández-Ramos A, Meana-Pañeda R (2008) Z Phys Chem 222:1291
Korolkov MV, Manz J, Paramonov GK (1996) J Chem Phys 105:10874
Došlić N, Kühn O, Manz J (1998) Ber Bunsenges Phys Chem 102:292
Waluk J, Muller M, Swiderek P, Kocher M, Vogel E, Hohlneicher G, Michl J (1991) J Am Chem Soc 113:5511
Parac M, Grimme S (2002) J Phys Chem A 106:6844
Sobolewski AL, Gil M, Dobkowski J, Waluk J (2009) J Phys Chem A 113:7714
Giese K, Petković M, Naundorf H, Kühn O (2006) Phys Rep 430:211
Waluk J (2006) Acc Chem Res 39:945
Waluk J (2009) Chem Phys Chem 10:761
Walewski L, Waluk J, Lesyng B (2010) J Phys Chem A 114:2313
Acknowledgments
This work has been in part financially supported by a scholarship from the Ministry of Higher Education of the Arab Republic of Egypt.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Abdel-Latif, M.K., Kühn, O. Laser control of double proton transfer in porphycenes: towards an ultrafast switch for photonic molecular wires. Theor Chem Acc 128, 307–316 (2011). https://doi.org/10.1007/s00214-010-0847-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00214-010-0847-y