Fluctuating exciton localization in giant π-conjugated spoked-wheel macrocycles

Nature Chemistry

Volumn 5, Issue 11, 2013, Pages 964-970

  Aggarwal, A Vikas ^a   Thiessen, Alexander ^b   Idelson, Alissa ^a   Kalle, Daniel ^a   Würsch, Dominik ^c   Stangl, Thomas ^c   Steiner, Florian ^c   Jester, Stefan S ^a   Vogelsang, Jan ^c   Höger, Sigurd ^a   Lupton, John M ^b,c  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; POLYMER;

CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; ARTICLE;

FLUORESCENCE RESONANCE ENERGY TRANSFER; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYMERS;

EID: 84887774864     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1758     Document Type: Article

References (48)

1. Scholes, G. D., Fleming, G. R., Olaya-Castro, A. & van Grondelle, R. Lessons from nature about solar light harvesting. Nature Chem. 3, 763-774 (2011).
2. Hwang, Í. & Scholes, G. D. Electronic energy transfer and quantum-coherence in p-conjugated polymers. Chem. Mater. 23, 610-620 (2011).
3. Lupton, J. M. Chromophores in conjugated polymers-all straight? Chem. Phys. Chem. 13, 901-907 (2012).
4. Hu, D. H. et al. Collapse of stiff conjugated polymers with chemical defects into ordered, cylindrical conformations. Nature 405, 1030-1033 (2000).
5. Schwartz, B. J. Conjugated polymers: what makes a chromophore? Nature Mater. 7, 427-428 (2008).
6. Schwartz, B. J. Conjugated polymers as molecular materials: how chain conformation and film morphology influence energy transfer and interchain interactions. Annu. Rev. Phys. Chem. 54, 141-172 (2003).
7. Bässler, H. & Schweitzer, B. Site-selective fluorescence spectroscopy of conjugated polymers and oligomers. Acc. Chem. Res. 32, 173-182 (1999).
8. Tempelaar, R., Stradomska, A., Knoester, J. & Spano, F. C. Anatomy of an exciton: vibrational distortion and exciton coherence in H- and J-aggregates. J. Phys. Chem. B 117, 457-466 (2013).
9. Lippitz, M. et al. Coherent electronic coupling versus localization in individual molecular dimers. Phys. Rev. Lett. 92, 103001 (2004).
10. Hernando, J. et al. Single molecule photobleaching probes the exciton wave function in a multichromophoric system. Phys. Rev. Lett. 93, 236404 (2004).
11. Tretiak, S., Saxenea, A., Martin, R. L. & Bishop, A. R. Conformational dynamics of photoexcited conjugated molecules. Phys. Rev. Lett. 89, 097402 (2002).
12. Ruseckas, A. et al. Ultrafast depolarization of the fluorescence in a conjugated polymer. Phys. Rev. B 72, 115214 (2005).
13. Mössinger, D., Hornung, J., Lei, S., De Feyter, S. & Höger, S. Molecularly defined shape-persistent 2D oligomers: the covalent-template approach to molecular spoked wheels. Angew. Chem. Ínt. Ed. 46, 6802-6806 (2007).
14. Mayor, M. & Didschies, C. A giant conjugated molecular ring. Angew. Chem. Ínt. Ed. 42, 3176-3179 (2003).
15. Mössinger, D. et al. Large all-hydrocarbon spoked wheels of high symmetry: modular synthesis, photophysical properties, and surface assembly. J. Am. Chem. Soc. 132, 1410-1423 (2010).
16. Jung, S. H. et al. A conjugated polycarbazole ring around a porphyrin. Angew. Chem. Ínt. Ed. 45, 4685-4690 (2006).
17. Simon, S. C., Schmaltz, B., Rouhanipour, A., Räder, H. J., & Müllen, K. A macrocyclic model dodecamer for polyfluorenes. Adv. Mater. 21, 83-85 (2009).
18. Arnold, L., Norouzi-Arasi, H., Wagner, M., Enkelmann, V. & Müllen, K. A porphyrin-related macrocycle from carbazole and pyridine building blocks: synthesis and metal coordination. Chem. Commun. 47, 970-972 (2011).
19. Cho, H. S. et al. Excitation energy transport processes of porphyrin monomer, dimer, cyclic trimer, and hexamer probed by ultrafast fluorescence anisotropy decay. J. Am. Chem. Soc. 125, 5849-5860 (2003).
20. Hori, T. et al. Giant porphyrin wheels with large electronic coupling as models of light-harvesting photosynthetic antenna. Chem. Eur. J. 12, 1319-1327 (2006).
21. Sprafke, J. K. et al. Belt-shaped p-systems: relating geometry to electronic structure in a six-porphyrin nanoring. J. Am. Chem. Soc. 133, 17262-17273 (2011).
22. O'Sullivan, M. C. et al. Vernier templating and synthesis of a 12-porphyrin nano-ring. Nature 469, 72-75 (2011).
23. Yang, J., Yoon, M. C., Yoo, H., Kim, P., & Kim, D. Excitation energy transfer in multiporphyrin arrays with cyclic architectures: towards artificial light-harvesting antenna complexes. Chem. Soc. Rev. 41, 4808-4826 (2012).
24. Hoffmann, M. et al. Enhanced p conjugation around a porphyrin[6] nanoring. Angew. Chem. Ínt. Ed. 47, 4993-4996 (2008).
25. Íyoda, M., Yamakawa, J. & Rahman, M. J. Conjugated macrocycles: concepts and applications. Angew. Chem. Ínt. Ed. 50, 10522-10553 (2011).
26. Kawase, T. & Kurata, H. Ball-, bowl-, and belt-shaped conjugated systems and their complexing abilities: exploration of the concave-convex p2p interaction. Chem. Rev. 106, 5250-5273 (2006).
27. Kawase, T. et al. Cyclic [5]paraphenyleneacetylene: synthesis, properties, and formation of a ring-in-ring complex showing a considerably large association constant and entropy effect. Angew. Chem. Ínt. Ed. 46, 1086-1088 (2007).
28. Höger, S. & Bonrad, K. 3-Cyanopropyl-dimethysilyl acetylene (CPDMS acetylene), a polar analogue of trimethylsilyl acetylene: synthesis and applications in the preparation of monoprotected bisacetylenes. J. Org. Chem. 65, 2243-2245 (2000).
29. Bednarz, M., Reineker, P., Mena-Osteritz, E. & Bäuerle, P. Optical absorption spectra of linear and cyclic thiophenes-selection rules manifestation. J. Lumin. 110, 225-231 (2004).
30. Bhaskar, A. et al. Enhancement of two-photon absorption cross-section in macrocyclic thiophenes with cavities in the nanometer regime. J. Phys. Chem. B 111, 946-954 (2007).
31. Mena-Osteritz, E., Zhang, F., Gotz, G., Reineker, P. & Bäuerle, P. Optical properties of fully conjugated cyclo[n]thiophenes-an experimental and theoretical approach. Beilstein J. Nanotech. 2, 720-726 (2011).
32. Varnavski, O., Bäuerle, P. & Goodson, T. Strong coupling in macrocyclic thiophene investigated by time-resolved two-photon excited fluorescence. Opt. Lett. 32, 3083-3085 (2007).
33. Zhang, F., Gotz, G., Winkler, H. D. F., Schalley, C. A. & Bäuerle, P. Giant cyclo[n]thiophenes with extended p conjugation. Angew. Chem. Ínt. Ed. 48, 6632-6635 (2009).
34. Kunz, R. et al. Exciton self trapping in photosynthetic pigment-protein complexes studied by single-molecule spectroscopy. J. Phys. Chem. B 116, 11017-11023 (2012).
35. Tretiak, S. & Mukamel, S. Density matrix analysis and simulation of electronic excitations in conjugated and aggregated molecules. Chem. Rev. 102, 3171-3212 (2002).
36. Tubasum, S., Cogdell, R. J., Scheblykin, Í. G. & Pullerits, T. Excitation-emission polarization spectroscopy of single light harvesting complexes. J. Phys. Chem. B 115, 4963-4970 (2011).
37. Tubasum, S., Thomsson, D., Cogdell, R., Scheblykin, Í. & Pullerits, T. Polarization single complex imaging of circular photosynthetic antenna. Photosyn. Res. 111, 41-45 (2012).
38. Bopp, M. A., Sytnik, A., Howard, T. D., Cogdell, R. J. & Hochstrasser, R. M. The dynamics of structural deformations of immobilized single light-harvesting complexes. Proc. Natl Acad. Sci. USA 96, 11271-11276 (1999).
39. Mirzov, O. et al. Polarization portraits of single multichromophoric systems: visualizing conformation and energy transfer. Small 5, 1877-1888 (2009).
40. Stangl, T. et al. Temporal switching of homo-FRET pathways in singlechromophore dimer models of p-conjugated polymers. J. Am. Chem. Soc. 135, 78-81 (2013).
41. Thomasson, D., Sforazzini, G., Anderson, H. L. & Scheblykin, Í. G. Excitation polarization provides structural resolution of individual non-blinking nano-objects. Nanoscale 5, 3070-3077 (2013).
42. Forster, M., Thomsson, D., Hania, P. R. & Scheblykin, Í. G. Redistribution of emitting state population in conjugated polymers probed by single-molecule fluorescence polarization spectroscopy. Phys. Chem. Chem. Phys. 9, 761-766 (2007).
43. Flors, C. et al. Energy and electron transfer in ethynylene bridged perylene diimide multichromophores. J. Phys. Chem. C 111, 4861-4870 (2007).
44. Feist, F. A., Tommaseo, G. & Basché, T. Observation of very narrow linewidths in the fluorescence excitation spectra of single conjugated polymer chains at 1.2. K. Phys. Rev. Lett. 98, 208301 (2007).
45. Schindler, F., Lupton, J. M., Feldmann, J. & Scherf, U. A universal picture of chromophores in p-conjugated polymers derived from single-molecule spectroscopy. Proc. Natl Acad. Sci. USA 101, 14695-14700 (2004).
46. Müller, J. G., Anni, M., Scherf, U., Lupton, J. M. & Feldmann, J. Vibrational fluorescence spectroscopy of single conjugated polymer molecules. Phys. Rev. B 70, 035205 (2004).
47. Wu, S. L., Liu, F., Shen, Y., Cao, J. S. & Silbey, R. J. Efficient energy transfer in light-harvesting systems, Í: optimal temperature, reorganization energy and spatial-temporal correlations. New J. Phys. 12, 105012 (2010).
48. Higgins, D. A., VandenBout, D. A., Kerimo, J. & Barbara, P. F. Polarizationmodulation near-field scanning optical microscopy of mesostructured materials. J. Phys. Chem. 100, 13794-13803 (1996).