Phthalocyanine-nanocarbon ensembles: From discrete molecular and supramolecular systems to hybrid nanomaterials

Accounts of Chemical Research

Volumn 48, Issue 4, 2015, Pages 900-910

  Bottari, Giovanni ^a,b   De La Torre, Gema ^a   Torres, Tomas ^a,b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84928333621     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5004384     Document Type: Article

References (51)

1. Special issue on Artificial Photosynthesis and Solar Fuels. Acc. Chem. Res. 2009, 42 (12).
2. The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2003; Vols. 15-20.
3. de la Torre, G.; Claessens, C. G.; Torres, T. Phthalocyanines: Old dyes, ne materials. Putting color in nanotechnology Chem. Commun. 2007, 2000-2015
4. Bottari, G.; de la Torre, G.; Guldi, D. M.; Torres, T. Covalent and noncovalent phthalocyanine-carbon nanostructure systems: Synthesis, Photoinduced electron transfer, and application to molecular photovoltaics Chem. Rev. 2010, 110, 6768-6816
5. de la Torre, G.; Bottari, G.; Sekita, S.; Hausmann, A.; Guldi, D. M.; Torres, T. A voyage into the synthesis and photophysics of homo- and heterobinuclear ensembles of phthalocyanines and porphyrins Chem. Soc. Rev. 2013, 42, 8049-8105
6. Fullerenes: Principles and Applications; Langa, F.; Nierengarten, J.-F., Eds.; Nanoscience and Nanotechnology Series; The Royal Society of Chemistry: Cambridge, U.K., 2007.
7. Iijima, S. Helical microtubules of graphitic carbon Nature 1991, 354, 56-58
8. Novoselov, K. S.; Geim, A. K.; Morozov, S. V.; Jiang, D.; Zhang, Y.; Dubonos, S. V.; Grigorieva, I. V.; Firsov, A. A. Electric field effect in atomically thin carbon films Science 2004, 306, 666-669
9. Durr, K.; Fiedler, S.; Linssen, T.; Hirsch, A.; Hanack, M. Synthesis and electrochemistry of Diels-Alder adducts of [60]fullerene ith a phthalocyanine and a hemiporphyrazine Chem. Ber. 1997, 130, 1375-1378
10. Chen, L.; Furukaa, K.; Gao, J.; Nagai, A.; Nakamura, T.; Dong, Y.; Jiang, D. Photoelectric covalent organic frameorks: Converting open lattices into ordered donor-acceptor heterojunctions J. Am. Chem. Soc. 2014, 136, 9806-9809
11. Pereira, A. M. V. M; Soares, A. R. M.; Hausmann, A.; Neves, M. G. P. M. S.; Tome, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Guldi, D. M.; Torres, T. Distorted fused porphyrin-phthalocyanine conjugates: Synthesis and photophysics of supramolecular assembled systems ith a pyridylfullerene Phys. Chem. Chem. Phys. 2011, 13, 11858-11863
12. Rodriguez-Morgade, M. S.; Plonska-Brzezinska, M. E.; Athans, A. J.; Carbonell, E.; de Miguel, G.; Guldi, D. M.; Echegoyen, L.; Torres, T. Synthesis, characterization, and photoinduced electron transfer processes of orthogonal ruthenium phthalocyanine fullerene assemblies J. Am. Chem. Soc. 2009, 131, 10484-10496
13. Garcia-Iglesias, M.; Peuntinger, K.; Kahnt, A.; Krausmann, J.; Vazquez, P.; González-Rodriguez, D.; Guldi, D. M.; Torres, T. Supramolecular assembly of multicomponent photoactive systems via cooperatively coupled equilibria J. Am. Chem. Soc. 2013, 135, 19311-19318
14. D'Souza, F.; Maligaspe, E.; Ohkubo, K.; Zandler, M. E.; Subbaiyan, N. K.; Fukuzumi, S. Photosynthetic reaction center mimicry: Lo reorganization energy driven charge stabilization in self-assembled cofacial zinc phthalocyanine dimer-fullerene conjugate J. Am. Chem. Soc. 2009, 131, 8787-8797
15. Ince, M.; Martinez-Diaz, M. V.; Barbera, J.; Torres, T. Liquid crystalline phthalocyanine-fullerene dyads J. Mater. Chem. 2011, 21, 1531-1536
16. 60 donor-acceptor dyads designed for molecular heterojunction photovoltaic devices Beilstein J. Org. Chem. 2009, 5 49 10.3762/bjoc.5.49
17. Kamei, T.; Kato, T.; Itoh, E.; Ohta, K. Discotic liquid crystals of transition metal complexes 47: Synthesis of phthalocyanine-fullerene dyads shoing spontaneous homeotropic alignment J. Porphyrins Phthalocyanines 2012, 16, 1261-1275
18. Hayashi, H.; Nihashi, W.; Umeyama, T.; Matano, Y.; Seki, S.; Shimizu, Y.; Imahori, H. Segregated donor-acceptor columns in liquid crystals that exhibit highly efficient ambipolar charge transport J. Am. Chem. Soc. 2011, 133, 10736-10739
19. 60 fullerene conjugate Ange. Chem., Int. Ed. 2008, 47, 2026-2031
20. 60 and copper phthalocyanine on Au(111): Self-organized nanostructuring Adv. Funct. Mater. 2001, 11, 175-178
21. 60 and phthalocyanines on a metal surface: Structural and electronic investigations J. Phys. Chem. C 2009, 113, 19373-19375
22. 60 cluster arrays J. Am. Chem. Soc. 2009, 131, 12026-12027
23. Calmettes, B.; Nagarajan, S.; Gourdon, A.; Abel, M.; Porte, L.; Coratger, R. Bicomponent supramolecular packing in flexible phthalocyanine netorks Ange. Chem., Int. Ed. 2008, 47, 6994-6998
24. Calmettes, B.; Nagarajan, S.; Gourdon, A.; Benjalal, Y.; Bouju, X.; Abel, M.; Porte, L.; Coratger, R. Properties of penta- tert -butylcorannulene molecules inserted in phthalocyanine netorks studied by lo-temperature scanning tunneling microscopy J. Phys. Chem. C 2009, 113, 21169-21176
25. Yoshimoto, S.; Honda, Y.; Ito, O.; Itaya, K. Supramolecular pattern of fullerene on 2D bimolecular chessboard consisting of bottom-up assembly of porphyrin and phthalocyanine molecules J. Am. Chem. Soc. 2008, 130, 1085-1092
26. 80 (M = Y, Sc) based dyads: Synthesis, and electrochemical, theoretical and photophysical studies Chem.-Eur. J. 2009, 15, 864-877
27. Stevenson, S.; Rice, G.; Glass, T.; Harlch, K.; Cromer, F.; Jordan, M. R.; Craft, J.; Hadju, E.; Bible, R.; Olmstead, M. M.; Maltra, K.; Fisher, A. J.; Balch, A. L.; Dorn, H. C. Small-bandgap endohedral metallofullerenes in high yield and purity Nature 1999, 401, 55-57
28. Tasis, D.; Tagmatarchis, N.; Bianco, A.; Prato, M. Chemistry of carbon nanotubes Chem. Rev. 2006, 106, 1105-1136
29. Dirian, K.; Herranz, M. A.; Katsukis, G.; Malig, J.; Rodríguez-Pérez, L.; Romero-Nieto, C.; Strauss, V.; Martín, N.; Guldi, D. M. Lo dimensional nanocarbons-chemistry and energy/electron transfer reactions Chem. Sci. 2013, 4, 4335-4353
30. Umeyama, T.; Imahori, H. Photofunctional hybrid nanocarbon materials J. Phys. Chem. C 2013, 117, 3195-3209
31. Ballesteros, B.; de la Torre, G.; Ehli, C.; Rahman, G. M. A.; Agullo-Rueda, F.; Guldi, D. M.; Torres, T. Single-all carbon nanotubes bearing covalently linked phthalocyanines-photoinduced electron transfer J. Am. Chem. Soc. 2007, 129, 5061-5068
32. Campidelli, S.; Ballesteros, B.; Filoramo, A.; Diaz Diaz, D.; de la Torre, G.; Torres, T.; Rahman, G. M. A.; Ehli, C.; Kiessling, D.; erner, F.; Sgobba, V.; Guldi, D. M.; Cioffi, C.; Prato, M.; Bourgoin, J.-P. Facile decoration of functionalized single-all carbon nanotubes ith phthalocyanines via click chemistry J. Am. Chem. Soc. 2008, 130, 11503-11509
33. Bekyarova, E.; Sarkar, S.; ang, F.; Itkis, M. E.; Kalinina, I.; Tian, X.; Haddon, R. C. Effect of covalent chemistry on the electronic structure and properties of carbon nanotubes and graphene Acc. Chem. Res. 2013, 46, 65-76
34. Le Ho, K. H.; Rivier, L.; Jousselme, B.; Jégou, P.; Filoramo, A.; Campidelli, S. Zn-porphyrin/Zn-phthalocyanine dendron for SNT functionalization Chem. Commun. 2010, 46, 8731-8733
35. 60 fullerene conjugates on individual carbon nanotubes Chem. Commun. 2010, 46, 4692-4694
36. Hahn, U.; Engmann, S.; Oelsner, C.; Ehli, C.; Guldi, D. M.; Torres, T. Immobilizing ater-soluble dendritic electron donors and electron acceptors-phthalocyanines and perylenediimides-onto single all carbon nanotubes J. Am. Chem. Soc. 2010, 132, 6392-6401
37. Bartelmess, J.; Ballesteros, B.; de la Torre, G.; Kiessling, D.; Campidelli, S.; Prato, M.; Torres, T.; Guldi, D. M. Phthalocyanine-pyrene conjugates: A poerful approach toard carbon nanotube solar cells J. Am. Chem. Soc. 2010, 132, 16202-16211
38. Ince, M.; Bartelmess, J.; Kiessling, D.; Dirian, K.; Martínez-Díaz, M. V.; Torres, T.; Guldi, D. M. Immobilizing NIR absorbing azulenocyanines onto single all carbon nanotubes-from charge transfer to photovoltaics Chem. Sci. 2012, 3, 1472-1480
39. Das, S. K.; Subbaiyan, N. K.; D'Souza, F.; Sandanayaka, A. S. D.; akahara, T.; Ito, O. Formation and photoinduced properties of zinc porphyrin-SCNT and zinc phthalocyanine-SCNT nanohybrids using diameter sorted nanotubes assembled via metal-ligand coordination and π-π stacking J. Porphyrins Phthalocyanines 2011, 15, 1033-1043
40. Sandanayaka, A. S. D.; Subbaiyan, N. K.; Das, S. K.; Chitta, R.; Maligaspe, E.; Hasobe, T.; Ito, O.; D'Souza, F. Diameter-sorted SCNT-porphyrin and SCNT-phthalocyanine conjugates for light-energy harvesting ChemPhysChem 2011, 12, 2266-2273
41. Bartelmess, J.; Ehli, C.; Cid, J.-J.; Garcia-Iglesias, M.; Vazquez, P.; Torres, T.; Guldi, D. M. Tuning and optimizing the intrinsic interactions beteen phthalocyanine-based PPV oligomers and single-all carbon nanotubes toard n-type/p-type Chem. Sci. 2011, 2, 652-660
42. Bartelmess, J.; Ehli, C.; Cid, J.-J.; Garcia-Iglesias, M.; Vazquez, P.; Torres, T.; Guldi, D. M. Screening interactions of zinc phthalocyanine-PPV oligomers ith single all carbon nanotubes-a comparative study J. Mater. Chem. 2011, 21, 8014-8020
43. Umeyama, T.; Tezuka, N.; Seki, S.; Matano, Y.; Nishi, M.; Hirao, K.; Lehtivuori, H.; Tkachenko, N. V.; Lemmetyinen, H.; Nakao, Y.; Sakaki, S.; Imahori, H. Selective formation and efficient photocurrent generation of [70]fullerene-single-alled carbon nanotube composites Adv. Mater. 2010, 22, 1767-1770
44. Hernandez, Y.; Nicolosi, V.; Lotya, M.; Blighe, F. M.; Sun, Z.; De, S.; McGovern, I. T.; Holland, B.; Byrne, M.; Gun'Ko, Y. K.; Boland, J. J.; Niraj, P.; Duesberg, G.; Krishnamurthy, S.; Goodhue, R.; Hutchison, J.; Scardaci, V.; Ferrari, A. C.; Coleman, J. N. High-yield production of graphene by liquid-phase exfoliation of graphite Nat. Nanotechnol. 2008, 3, 563-568
45. Ragoussi, M.-E.; Malig, J.; Katsukis, G.; Butz, B.; Spiecker, E.; de la Torre, G.; Torres, T.; Guldi, D. M. Linking photo- and redox-active phthalocyanines covalently to graphene Ange. Chem., Int. Ed. 2012, 51, 6421-6425
46. Malig, J.; Jux, N.; Guldi, D. M. Toard multifunctional et chemically functionalized graphene; integration of oligomeric, molecular, and particulate building blocks that reveal photoactivity and redox activity Acc. Chem. Res. 2013, 46, 53-64
47. Malig, J.; Jux, N.; Kiessling, D.; Cid, J.-J.; Vazquez, P.; Torres, T.; Guldi, D. M. Toards tunable graphene/phthalocyanine-PPV hybrid systems Ange. Chem., Int. Ed. 2011, 50, 3561-3565
48. Brinkhaus, L.; Katsukis, G.; Malig, J.; Costa, R. D.; Garcia-Iglesias, M.; Vazquez, P.; Torres, T.; Guldi, D. M. Tuning the stability of graphene layers by phthalocyanine-based o -PPV oligomers toards photo- and redoxactive materials Small 2013, 9, 2348-2357
49. Das, S. K.; KC, C. B.; Ohkubo, K.; Yamada, Y.; Fukuzumi, S.; D'Souza, F. Decorating single layer graphene oxide ith electron donor and acceptor molecules for the study of photoinduced electron transfer Chem. Commun. 2013, 49, 2013-2015
50. Ragoussi, M.-E.; Katsukis, G.; Roth, A.; Malig, J.; de la Torre, G.; Torres, T.; Guldi, D. M. Electron-donating behavior of fe-layer graphene in covalent ensembles ith electron-accepting phthalocyanines J. Am. Chem. Soc. 2014, 136, 4593-4598
51. Roth, A.; Ragoussi, M.-E.; ibmer, L.; Katsukis, G.; de la Torre, G.; Torres, T.; Guldi, D. M. Electron-accepting phthalocyanine-pyrene conjugates: Toards liquid phase exfoliation of graphite and photoactive nanohybrid formation ith graphene Chem. Sci. 2014, 5, 3432-3438