π-Conjugation and End Group Effects in Long Cumulenes: Raman Spectroscopy and DFT Calculations

Journal of Physical Chemistry C

Volumn 118, Issue 45, 2014, Pages 26415-26425

  Tommasini, Matteo ^a   Milani, Alberto ^a   Fazzi, Daniele ^b   Lucotti, Andrea ^a   Castiglioni, Chiara ^a   Januszewski, Johanna A ^c   Wendinger, Dominik ^c   Tykwinski, Rik R ^c  

^a POLITECNICO DI MILANO   (Italy)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BOND LENGTH; CHAINS; CHARACTERIZATION; GRAPHENE; HYBRID MATERIALS; RAMAN SPECTROSCOPY; SELF ASSEMBLY;

BOND LENGTH ALTERNATION; ELECTRON CONJUGATION; IR AND RAMAN SPECTRA; MOLECULAR PROPERTIES; RAMAN INTENSITIES; SPECTROSCOPIC PARAMETERS; SPECTROSCOPIC PROPERTY; STRUCTURAL COUPLING;

DENSITY FUNCTIONAL THEORY;

EID: 84929380973     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp509724d     Document Type: Article

References (61)

1. Shi Shun, A. L. K.; Tykwinski, R. R. Synthesis of Naturally Occurring Polyynes Angew. Chem., Int. Ed. 2006, 45, 1034-1057
2. Pan, Y.; Lowary, T. L.; Tykwinski, R. R. Naturally Occurring and Synthetic Polyyne Glycosides Can. J. Chem. 2009, 87, 1565-1582
3. Gung, B. W. Total Synthesis of Polyyne Natural Products C. R. Chim. 2009, 12, 489-505
4. Whittaker, A. G.; Watts, E. J.; Lewis, R. S.; Anders, E. Carbynes: Carriers of Primordial Noble Gases in Meteorites Science 1980, 209, 1512-1514
5. Hayatsu, R.; Scott, R. G.; Studier, M. H.; Lewis, R. S.; Anders, E. Carbynes in Meteorites: Detection, Low-Temperature Origin, and Implications for Interstellar Molecules Science 1980, 209, 1515-1518
6. Webster, A. Carbyne as a Possible Constituent of the Interstellar Dust Mon. Not. R. Astron. Soc. 1980, 192, 7-9
7. Ravagnan, L.; Siviero, F.; Lenardi, C.; Piseri, P.; Barborini, E.; Milani, P.; Casari, C. S.; Li Bassi, A.; Bottani, C. E. Cluster-Beam Deposition and in situ Characterization of Carbyne-Rich Carbon Films Phys. Rev. Lett. 2002, 89, 285506
8. Ravagnan, L.; Piseri, P.; Bruzzi, M.; Miglio, S.; Bongiorno, G.; Baserga, A.; Casari, C. S.; Li Bassi, A.; Lenardi, C.; Yamaguchi, Y. Influence of Cumulenic Chains on the Vibrational and Electronic Properties of sp-sp 2 Amorphous Carbon Phys. Rev. Lett. 2007, 98, 216103
9. Casari, C. S.; Li Bassi, A.; Baserga, A.; Ravagnan, L.; Piseri, P.; Lenardi, C.; Tommasini, M.; Milani, A.; Fazzi, D.; Bottani, C. E. Low-Frequency Modes in the Raman Spectrum of sp-sp 2 Nanostructured Carbon Phys. Rev. B 2008, 77, 195444
10. Zhao, X.; Ando, Y.; Liu, Y.; Jinno, M.; Suzuki, T. Carbon Nanowire Made of a Long Linear Carbon Chain Inserted Inside a Multiwalled Carbon Nanotube Phys. Rev. Lett. 2003, 90, 187401
11. Scuderi, V.; Scalese, S.; Bagiante, S.; Compagnini, G.; DUrso, L.; Privitera, V. Direct Observation of the Formation of Linear C Chain/Carbon Nanotube Hybrid Systems Carbon 2009, 47, 2134-2137
12. Jin, C.; Lan, H.; Peng, L.; Suenaga, K.; Iijima, S. Deriving Carbon Atomic Chains from Graphene Phys. Rev. Lett. 2009, 102, 205501
13. Lagow, R. J.; Kampa, J. J.; Wei, H.-C.; Battle, S. L.; Genge, J. W.; Laude, D. A.; Harper, C. J.; Bau, R.; Stevens, R. C.; Haw, J. F. Synthesis of Linear Acetylenic Carbon: The sp Carbon Allotrope Science 1995, 267, 362-367
14. Cataldo, F. Polyynes and Cyanopolyynes Synthesis from the Submerged Electric Arc: about the Role Played by the Electrodes and Solvents in Polyynes Formation Tetrahedron 2004, 60, 4265-4274
15. Cataldo, F., Ed. Polyynes: Synthesis, Properties and Applications; CRC Taylor & Francis: Boca Raton, FL, 2006.
16. Cataldo, F.; Casari, C. S. Synthesis, Structure and Thermal Properties of Copper and Silver Polyynides and Acetylides J. Inorg. Organomet. Polym. Mater. 2007, 17, 641-651
17. Chalifoux, W. A.; Tykwinski, R. R. Synthesis of Polyynes To Model the sp-Carbon Allotrope Carbyne Nat. Chem. 2010, 2, 967-971
18. Sato, Y.; Kodama, T.; Shiromaru, H.; Sanderson, J.; Fujino, T.; Wada, Y.; Wakabayashi, T.; Achiba, Y. Synthesis of Polyyne Molecules from Hexane by Irradiation of Intense Femtosecond Laser Pulses Carbon 2010, 48, 1673-1676
19. Wesolowski, M.; Kuzmin, S.; Moores, B.; Wales, B.; Karimi, R.; Zaidi, A.; Leonenko, Z.; Sanderson, J.; Duley, W. Polyyne Synthesis and Amorphous Carbon Nano-Particle Formation by Femtosecond Irradiation of Benzene Carbon 2011, 49, 625-630
20. Hu, A.; Rybachuk, M.; Lu, Q.-B.; Duley, W. W. Direct Synthesis of sp-Bonded Carbon Chains on Graphite Surface by Femtosecond Laser Irradiation Appl. Phys. Lett. 2007, 91, 131906
21. Heimann, R. B.; Evsyukov, S. E.; Kavan, L., Eds. Carbyne and Carbynoid Structures; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999.
22. Szafert, S.; Gladysz, J. A. Carbon in One Dimension: Structural Analysis of the Higher Conjugated Polyynes. Chem. Rev. 2003, 103, 4175-4206, PMID: 14611262.
23. Chalifoux, W. A.; Tykwinski, R. R. Synthesis of Extended Polyynes: Toward Carbyne C. R. Chim. 2009, 12, 341-358
24. Januszewski, J. A.; Wendinger, D.; Methfessel, C. D.; Hampel, F.; Tykwinski, R. R. Synthesis and Structure of Tetraarylcumulenes: Characterization of Bond-Length Alternation versus Molecule Length Angew. Chem., Int. Ed. 2013, 52, 1817-1821
25. Januszewski, J. A.; Tykwinski, R. R. Synthesis and Properties of Long [n]Cumulenes (n ≥5) Chem. Soc. Rev. 2014, 43, 3184-3203
26. Ravagnan, L.; Manini, N.; Cinquanta, E.; Onida, G.; Sangalli, D.; Motta, C.; Devetta, M.; Bordoni, A.; Piseri, P.; Milani, P. Effect of Axial Torsion on sp-Carbon Atomic Wires Phys. Rev. Lett. 2009, 102, 245502
27. Innocenti, F.; Milani, A.; Castiglioni, C. Can Raman Spectroscopy Detect Cumulenic Structures of Linear Carbon Chains? J. Raman Spectrosc. 2010, 41, 226-236
28. Milani, A.; Lucotti, A.; Russo, V.; Tommasini, M.; Cataldo, F.; Li Bassi, A.; Casari, C. S. Charge Transfer and Vibrational Structure of sp-Hybridized Carbon Atomic Wires Probed by Surface Enhanced Raman Spectroscopy J. Phys. Chem. C 2011, 115, 12836-12843
29. Yildizhan, M. M.; Fazzi, D.; Milani, A.; Brambilla, L.; Del Zoppo, M.; Chalifoux, W. A.; Tykwinski, R. R.; Zerbi, G. Photogenerated Cumulenic Structure of Adamantyl Endcapped Linear Carbon Chains: An Experimental and Computational Investigation Based on Infrared Spectroscopy J. Chem. Phys. 2011, 134, 124512
30. Lang, N. D.; Avouris, P. Carbon-Atom Wires: Charge-Transfer Doping, Voltage Drop, and the Effect of Distortions Phys. Rev. Lett. 2000, 84, 358-361
31. Crljen, Z.; Baranovic, G. Unusual Conductance of Polyyne-Based Molecular Wires Phys. Rev. Lett. 2007, 98, 116801
32. Liu, M.; Artyukhov, V. I.; Lee, H.; Xu, F.; Yakobson, B. I. Carbyne from First Principles: Chain of C Atoms, a Nanorod or a Nanorope ACS Nano 2013, 7, 10075-10082
33. Ermer, S. P.; Lovejoy, S. M.; Leung, D. S.; Altman, J. C.; Aron, K. P.; Spitzer, R. C.; Hansen, G. A. Synthesis and Evaluation of Cumulenes: Novel Rigid Nonlinear Optical Molecules Proc. SPIE 1990, 1337, 89-98
34. Kminek, I.; Klimovic, J.; Prasad, P. N. Third-Order Nonlinear Optical Response of Some Tetrasubstituted Cumulenes Chem. Mater. 1993, 5, 357-360
35. Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. Polyynes as a Model for Carbyne: Synthesis, Physical Properties, and Nonlinear Optical Response. J. Am. Chem. Soc. 2005, 127, 2666-2676, PMID: 15725024.
36. Lucotti, A.; Tommasini, M.; Fazzi, D.; Del Zoppo, M.; Chalifoux, W. A.; Tykwinski, R. R.; Zerbi, G. Absolute Raman Intensity Measurements and Determination of the Vibrational Second Hyperpolarizability of Adamantyl Endcapped Polyynes J. Raman Spectrosc. 2012, 43, 1293-1298
37. Lang, N. D.; Avouris, P. Oscillatory Conductance of Carbon-Atom Wires Phys. Rev. Lett. 1998, 81, 3515-3518
38. Ballmann, S.; Hieringer, W.; Secker, D.; Zheng, Q.; Gladysz, J. A.; Görling, A.; Weber, H. B. Molecular Wires in Single-Molecule Junctions: Charge Transport and Vibrational Excitations ChemPhysChem 2010, 11, 2256-2260
39. Börrnert, F.; Börrnert, C.; Gorantla, S.; Liu, X.; Bachmatiuk, A.; Joswig, J.-O.; Wagner, F. R.; Schäffel, F.; Warner, J. H.; Schönfelder, R. Single-Wall-Carbon-Nanotube/Single-Carbon-Chain Molecular Junctions Phys. Rev. B 2010, 81, 085439
40. Nair, A. K.; Cranford, S. W.; Buehler, M. J. The Minimal Nanowire: Mechanical Properties of Carbyne Europhys. Lett. 2011, 95, 16002
41. Akdim, B.; Pachter, R. Switching Behavior of Carbon Chains Bridging Graphene Nanoribbons: Effects of Uniaxial Strain ACS Nano 2011, 5, 1769-1774
42. Ataca, C.; Ciraci, S. Perpendicular Growth of Carbon Chains on Graphene from First-Principles Phys. Rev. B 2011, 83, 235417
43. Moreno-Garca, P.; Gulcur, M.; Manrique, D. Z.; Pope, T.; Hong, W.; Kaliginedi, V.; Huang, C.; Batsanov, A. S.; Bryce, M. R.; Lambert, C. Single-Molecule Conductance of Functionalized Oligoynes: Length Dependence and Junction Evolution J. Am. Chem. Soc. 2013, 135, 12228-12240
44. Cretu, O.; Botello-Mendez, A. R.; Janowska, I.; Pham-Huu, C.; Charlier, J.-C.; Banhart, F. Electrical Transport Measured in Atomic Carbon Chains Nano Lett. 2013, 13, 3487-3493
45. Prasongkit, J.; Grigoriev, A.; Ahuja, R. Mechano-Switching Devices from Carbon Wire-Carbon Nanotube Junctions Phys. Rev. B 2013, 87, 155434
46. Rivelino, R.; dos Santos, R. B.; de Brito Mota, F.; Gueorguiev, G. K. Conformational Effects on Structure, Electron States, and Raman Scattering Properties of Linear Carbon Chains Terminated by Graphene-Like Pieces J. Phys. Chem. C 2010, 114, 16367-16372
47. Tabata, H.; Fujii, M.; Hayashi, S.; Doi, T.; Wakabayashi, T. Raman and Surface-Enhanced Raman Scattering of a Series of Size-Separated Polyynes Carbon 2006, 44, 3168-3176
48. Wakabayashi, T.; Murakami, T.; Nagayama, H.; Nishide, D.; Kataura, H.; Achiba, Y.; Tabata, H.; Hayashi, S.; Shinohara, H. Raman Spectral Features of Longer Polyynes HC2 nH (n = 4-8) in SWNTs Eur. Phys. J. D 2009, 52, 79-82
49. Wada, Y.; Morisawa, Y.; Wakabayashi, T. Spectroscopic Characterization of a Series of Polyyne-Iodine Molecular Complexes H(CC)nH(I6) of n = 5-9 Chem. Phys. Lett. 2012, 541, 54-59
50. Agarwal, N. R.; Lucotti, A.; Fazzi, D.; Tommasini, M.; Castiglioni, C.; Chalifoux, W.; Tykwinski, R. R. Structure and Chain Polarization of Long Polyynes Investigated with Infrared and Raman Spectroscopy J. Raman Spectrosc. 2013, 44, 1398-1410
51. Lucotti, A.; Tommasini, M.; Fazzi, D.; Del Zoppo, M.; Chalifoux, W. A.; Ferguson, M. J.; Zerbi, G.; Tykwinski, R. R. Evidence for Solution-State Nonlinearity of sp-Carbon Chains Based on IR and Raman Spectroscopy: Violation of Mutual Exclusion J. Am. Chem. Soc. 2009, 131, 4239-4244
52. Yang, S.; Kertesz, M. Bond Length Alternation and Energy Band Gap of Polyyne. J. Phys. Chem. A 2006, 110, 9771-9774, PMID: 16884210.
53. Milani, A.; Tommasini, M.; Del Zoppo, M.; Castiglioni, C.; Zerbi, G. Carbon Nanowires: Phonon and π-Electron Confinement Phys. Rev. B 2006, 74, 153418
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09, Revision D.01; Gaussian Inc.: Wallingford, CT, 2009.
55. Castiglioni, C.; Tommasini, M.; Zerbi, G. Raman Spectroscopy of Polyconjugated Molecules and Materials: Confinement Effect in One and Two Dimensions Philos. Trans. R. Soc. A 2004, 362, 2425-2459
56. Radice, S.; Tommasini, M.; Castiglioni, C. Two Dimensional Correlation Raman Spectroscopy of Perfluoropolyethers: Effect of Peroxide Groups J. Mol. Struct. 2010, 974, 73-79
57. Johannessen, C.; Blanch, E. W.; Villani, C.; Abbate, S.; Longhi, G.; Agarwal, N. R.; Tommasini, M.; Lightner, D. A.; Raman, R. O. A. Spectra of - and (+)-2-Br-Hexahelicene: Experimental and DFT Studies of a π-Conjugated Chiral System J. Phys. Chem. B 2013, 117, 2221-2230
58. Tykwinski, R. R.; Chalifoux, W.; Eisler, S.; Lucotti, A.; Tommasini, M.; Fazzi, D.; Del Zoppo, M.; Zerbi, G. Toward Carbyne: Synthesis and Stability of Really Long Polyynes Pure Appl. Chem. 2010, 82, 891-904
59. Castiglioni, C.; Lopez Navarrete, J.; Zerbi, G.; Gussoni, M. A Simple Interpretation of the Vibrational Spectra of Undoped, Doped and Photoexcited Polyacetylene: Amplitude Mode Theory in the GF Formalism Solid State Commun. 1988, 65, 625-630
60. Castiglioni, C. In Vibrational Spectroscopy of Polymers: Principles and Practice; Everall, N.; Griffiths, P. R.; Chalmers, J. M., Eds.; Wiley: 2007.
61. Tommasini, M.; Castiglioni, C.; Zerbi, G. Raman Scattering of Molecular Graphenes Phys. Chem. Chem. Phys. 2009, 11, 10185-10194