Article
Macromolecules, Vol. 43, No. 18, 2010 7433
University are acknowledged for financial support. Computa-
tional resources and services used in this work were provided by
Ghent University. L.H. thanks the Spanish Ministry of Educa-
tion (Programa Nacional de Movilidad de Recursos Humanos
del Plan Nacional de I-Dþi 2008-2011) and the Spanish Science
and Innovation Ministry (MAT2008-06725-C03-02) for financial
support.
(22) Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405.
(23) Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
(24) Papajak, E.; Leverentz, H. R.; Zheng, J.; Truhlar, D. G. J. Chem.
Theory Comput. 2009, 5, 1197.
(25) Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
(26) Kormos, B. L.; Cramer, C. J. J. Phys. Org. Chem. 2002, 15, 712.
(27) (a) Wynne-Jones, W. F. K.; Eyring, H. J. J. Chem. Phys. 1936, 3,
492. (b) Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1935, 31,
875. (c) Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1937,
33, 448.
(28) (a) Ghysels, A.; Verstraelen, T.; Hemelsoet, K.; Waroquier, M.;
Van Speybroeck, V. J. Chem. Inf. Model., 2010, in revision.
(29) da Silva, E. F.; Svendsen, H. F.; Merz, K. M. J. Phys. Chem. A
2009, 113, 6404.
Supporting Information Available: Cartesian coordinates of
B3LYP/6-31þG(d,p) optimized geometries of all reactants,
transition states and products; imaginary and low frequency
modes of transition states; the experimental setup of the UV-vis
stop flow accessory. This material is available free of charge via
(30) Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 2006,
110, 2493.
(31) Pliego, J. R.; Riveros, J. M. J. Phys. Chem. A 2001, 105, 7241.
(32) Kamerlin, S. C. L.; Haranczyk, M.; Warshel, A. ChemPhysChem
2009, 10, 1125.
(33) De Sterck, B.; Vaneerdeweg, R.; Du Prez, F.; Waroquier, M.; Van
Speybroeck, V. Macromolecules 2010, 43, 827.
References and Notes
(1) (a) Shirakawa, J.; Louis, E. J.; MacDiarmid, A. G.; Chiang, C. K.;
Heeger, A. J. J. Chem. Soc., Chem. Commun. 1977, 578. (b) Kraft,
A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37,
ꢀ
403. (c) Thompson, B. C.; Frechet, J. M. J. Angew. Chem., Int. Ed.
2008, 47, 58.
(34) Chemical Reactor Theory: An Introduction; Denbigh, K. G., Turner,
J. C. R., Eds.; Cambridge University Press: Great Britain, 1971; p 30.
(35) Izgorodina, E. I.; Coote, M. L. Chem. Phys. 2006, 324, 96.
(36) Yu, X. R.; Pfaendtner, J.; Broadbelt, L. J. J. Phys. Chem. A 2008,
112, 6772.
(2) Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.;
Friend, R. H.; Holmes, A. B. Nature 1990, 347, 539.
(3) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55.
(4) Gilch, H. G.; Wheelwright, W. L. J. Polym. Sci., Part A: Polym.
Chem. 1966, 4, 1337.
(37) Van Cauter, K.; Van Speybroeck, V.; Waroquier, M. Chem-
PhysChem 2007, 8, 541.
(5) Louwet, F.; Vanderzande, D.; Gelan, J.; Mullens, J. Macromole-
cules 1995, 28, 1330.
(6) Son, S.; Dodabalapur, A.; Lovinger, A. J.; Galvin, M. E. Science
1995, 269, 376.
(38) Hemelsoet, K.; Van Durme, F.; Van Speybroeck, V.; Van Reyniers,
M.-F.; Van Waroquier, M. J. Phys. Chem. A 2010, 114, 2864
(39) Hemelsoet, K.; Van Speybroeck, V.; Waroquier, M. J. Phys. Chem.
A 2008, 112, 13566.
(7) (a) Henckens, A.; Duyssens, I.; Lutsen, L.; Vanderzande, D.; Cleij,
T. J. Polymer 2006, 47, 123. (b) Vandenbergh, J.; Wouters, J.;
Adriaensens, P. J.; Mens, R.; Cleij, T. J.; Lutsen, L.; Vanderzande,
D. J. M. Macromolecules 2009, 42, 3661.
(40) Bauschlicher, C. W., Jr.; Partridge, H. Chem. Phys. Lett. 1995, 240,
533.
(41) (a) Bell, R. D.; Wilson, A. K. Chem. Phys. Lett. 2004, 394, 105. (b)
Yockel, S.; Wilson, A. K. Chem. Phys. Lett. 2006, 429, 645.
(42) Denis, P. A.; Ventura, O. N. Chem. Phys. Lett. 2001, 344, 221.
(43) Stoffregen, S. A.; McCulla, R. D.; Wilson, R.; Cercone, S.; Miller,
J.; Jenks, W. S. J. Org. Chem. 2007, 72, 8235.
(44) Jiang, S.; Wang, Z.; Zhou, J.; Wen, Z.; Cen., K. J. Zhejiang Univ.,
Sci., A 2009, 10 (9), 1327.
(45) Cramer, C. J.; Truhlar, D. G. In Solvent Effects and Chemical
Reactivity; Kluwer: Dordrecht, 1996; pp 1-80.
(46) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
(47) Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2004, 1, 70.
(48) D’hooghe, M.; Van Speybroeck, V.; Van Nieuwenhove, A.;
Waroquier, M.; De Kimpe, N. J. Org. Chem. 2007, 72, 4733.
(49) D’hooghe, M.; Van Speybroeck, V.; Waroquier, M.; De Kimpe, N.
Chem. Commun. 2006, 1554.
(8) (a) Cho, B. R.; Kim, Y. K.; Han, M. S. Macromolecules 1998, 31,
2098. (b) Cho, B. R.; Kim, T. H.; Kim, Y. K.; Kim, N. S. Macro-
molecules 1999, 32, 3583. (c) Cho, B. R.; Kim, T. H.; Son, K. H.; Kim,
Y. K.; Lee, Y. K.; Jeon, S. J. Macromolecules 2000, 33, 8167.
(9) Van Breemen, A. J. J. M.; Issaris, A. C. J.; de Kok, M. M.; Van Der
Borght, M. J. A. N.; Adriaensens, P. J.; Gelan, J. M. J. V.;
Vanderzande, D. J. M. Macromolecules 1999, 32, 5728.
(10) Vanderzande, D.; Issaris, A.; Van Der Borght, M.; van Breemen,
A.; de Kok, M.; Gelan, J. Macromol. Symp. 1997, 125, 189.
(11) (a) Gillissen, S. PhD Dissertation, LUC Diepenbeek, Belgium,
2002.(b) Gillissen, S.; Lutsen, L.; Vanderzande, D.; Gelan, J. Synth.
Met. 2001, 119, 137.
(12) Gaussian 03, Revision D.01: Frisch, M. J.; Trucks, G. W.; Schlegel,
H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery,
J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.;
Iyengar, S. S.; Tomasi, J.;Barone, V. etal. Gaussian, Inc., Pittsburgh,
PA, 2003.
(50) Catak, S.; D’hooghe, M.; De Kimpe, N.; Waroquier, M.; Van
Speybroeck, V. J. Org. Chem. 2009, 75, 885.
(51) Catak, S.; D’hooghe, M.; Verstraelen, T.; Hemelsoet, K.; Van
Nieuwenhove, A.; Ha, H.; Waroquier, M.; De Kimpe, N.; Van
Speybroeck, V. J. Org. Chem., 2010, 75 (13), 4530.
(52) Catak, S.; Monard, G.; Aviyente, V.; Ruiz-Lopez, M. F. J. Phys.
Chem. A 2006, 110, 8354.
(13) Verstraelen, T.; Van Speybroeck, V.; Waroquier, M. J. Chem. Inf.
Model. 2008, 48 (7), 1530.
(14) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
(15) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
(16) Qingping, L.; Hongbing, J. I.; Shushen, L. V. Int. J. Quantum
Chem. 2009, 109, 448.
(17) (a) Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys.
Chem. A 2000, 104, 4811. (b) Lynch, B. J.; Zhao, Y.; Truhlar, D. G.
J. Phys. Chem. A 2003, 107, 1384.
(53) Van Speybroeck, V.; Moonen, K.; Hemelsoet, K.; Stevens, C. V.;
Waroquier, M. J. Am. Chem. Soc. 2006, 128, 8468.
(54) Catak, S.; Monard, G.; Aviyente, V.; Ruiz-Lopez, M. F. J. Phys.
Chem. A 2008, 112, 8752.
(55) Catak, S.; Monard, G.; Aviyente, V.; Ruiz-Lopez, M. F. J. Phys.
Chem. A 2009, 113, 1111.
(18) Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
(56) Schwalm, T.; Wiesecke, J.; Immel, S.; Rehahn., M. Macromolecules
2007, 40, 8842.
(57) Schwalm, T.; Wiesecke, J.; Immel, S.; Rehahn., M. Macromol.
(19) Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
(20) Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6908.
(21) Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158.
Rapid Commun. 2009, 30, 1295.