Energies of electronic transitions of pentaerythritol tetranitrate molecules and crystals

Journal of Physical Chemistry C

Volumn 118, Issue 18, 2014, Pages 9324-9335

  Tsyshevsky, Roman V ^a   Sharia, Onise ^a   Kuklja, Maija M ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC STRUCTURE; MEDICAL APPLICATIONS; MOLECULES;

CHARGE TRANSFER EXCITONS; CONDENSED ENERGETIC MATERIALS; ELECTRONIC TRANSITION; INITIATION PROCESS; LOW-ENERGY EXCITATIONS; NITRATE DECOMPOSITION; PENTAERYTHRITOL TETRANITRATE; SINGLET AND TRIPLET EXCITONS;

EXCITONS;

EID: 84900436243     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp500011a     Document Type: Article

References (79)

1. Naddo, T.; Che, Y.; Zhang, W.; Balakrishnan, K.; Yang, X.; Yen, M.; Zhao, J.; Moore, J. S.; Zang, L. Detection of Explosives with a Fluorescent Nanofibril Film J. Am. Chem. Soc. 2007, 129, 6978-6979
2. 2+ Nanocrystals for Fluorescence Detection of Trace TNT Explosive Anal. Chem. 2008, 80, 3458-3465
3. Kartha, K. K.; Babu, S. S.; Srinivasan, S.; Ajayaghosh, A. Attogram Sensing of Trinitrotoluene with a Self-Assembled Molecular Gelator J. Am. Chem. Soc. 2012, 134, 4834-4841
4. Pramanik, S.; Zheng, C.; Zhang, X.; Emge, T. J.; Li, J. New Microporous Metal-Organic Framework Demonstrating Unique Selectivity for Detection of High Explosives and Aromatic Compounds J. Am. Chem. Soc. 2011, 133, 4153-4155
5. Yang, J.-S.; Swager, T. M. Porous Shape Persistent Fluorescent Polymer Films: An Approach to TNT Sensory Materials J. Am. Chem. Soc. 1998, 120, 5321-5322
6. Sohn, H.; Sailor, M. J.; Magde, D.; Trogler, W. C. Detection of Nitroaromatic Explosives Based on Photoluminescent Polymers Containing Metalloles J. Am. Chem. Soc. 2003, 125, 3821-3830
7. Germain, M. E.; Knapp, M. J. Discrimination of Nitroaromatics and Explosives Mimics by a Fluorescent Zn(salicylaldimine) Sensor Array J. Am. Chem. Soc. 2008, 130, 5422-5423
8. Li, Z.; Ding, J.; Song, N.; Lu, J.; Tao, Y. Development of a New s-Tetrazine-Based Copolymer for Efficient Solar Cells J. Am. Chem. Soc. 2010, 132, 13160-13161
9. Pinnaduwage, L. A.; Gehl, A.; Hedden, D. L.; Muralidharan, G.; Thundat, T.; Lareau, R. T.; Sulchek, T.; Manning, L.; Rogers, B.; Jones, M. Explosives: A Microsensor for Trinitrotoluene Vapour Nature 2003, 425, 474
10. Moore, D. S. Recent Advances in Trace Explosives Detection Instrumentation Sens. Imaging 2007, 8, 9-38
11. Rose, A.; Zhu, Z.; Madigan, C. F.; Swager, T. M.; Bulovic, V. Sensitivity Gains in Chemosensing by Lasing Action in Organic Polymers Nature 2005, 434, 876-879
12. Andrew, T. L.; Swager, T. M. A Fluorescence Turn-On Mechanism to Detect High Explosives RDX and PETN J. Am. Chem. Soc. 2007, 129, 7254-7255
13. Germain, M. N.; Arechederra, R. L.; Minteer, S. D. Nitroaromatic Actuation of Mitochondrial Bioelectrocatalysis for Self-Powered Explosive Sensors J. Am. Chem. Soc. 2008, 130, 15272-15273
14. Malashikhin, S.; Finney, N. S. Fluorescent Signaling Based on Sulfoxide Profluorophores: Application to the Visual Detection of the Explosive TATP J. Am. Chem. Soc. 2008, 130, 12846-12847
15. Zhang, K.; Zhou, H.; Mei, Q.; Wang, S.; Guan, G.; Liu, R.; Zhang, J.; Zhang, Z. Instant Visual Detection of Trinitrotoluene Particulates on Various Surfaces by Ratiometric Fluorescence of Dual-Emission Quantum Dots Hybrid J. Am. Chem. Soc. 2011, 133, 8424-8427
16. Evans, B. L.; Yoffe, A. D. Structure and Stability of Inorganic Azides. II. Some Physical and Optical Properties, and the Fast Decomposition of Solid Monovalent Inorganic Azides Proc. R. Soc. London, Ser. A 1959, 250, 346-366
17. Bernstein, E. R. In Overviews of Recent Research on Energetic Materials; Shaw, R.; Brill, T.; Thompson, D., Eds.; World Scientific: Singapore, 2004; pp 161-190.
18. Kunz, A. B.; Kuklja, M. M.; Botcher, T. R.; Russel, T. P. Initiation of Chemistry in Molecular Solids by Processes Involving Electronic Excited States Thermochim. Acta 2002, 384, 279-284
19. Kitaigorodskii, A. I. Organic Chemical Crystallography; Consultants Bureau: New York, 1958; pp 120-124, 216-217, and 263-264.
20. Gruzdkov, Y. A.; Gupta, Y. M. Vibrational Properties and Structure of Pentaerythritol Tetranitrate J. Phys. Chem. A 2001, 105, 6197-6202
21. Zhurova, E. A.; Stash, A. I.; Tsirelson, V. G.; Zhurov, V. V.; Bartashevich, E. V.; Potemkin, V. A.; Pinkerton, A. A. Atoms-in-Molecules Study of Intra- and Intermolecular Bonding in the Pentaerythritol Tetranitrate Crystal J. Am. Chem. Soc. 2006, 128, 14728-14734
22. 4 J. Am. Chem. Soc. 2007, 129, 6908-6915
23. Liu, W.-G.; Zybin, S. V.; Dasgupta, S.; Klapötke, T. M.; Goddard, W. A., III. Explanation of the Colossal Detonation Sensitivity of Silicon Pentaerythritol Tetranitrate (Si-PETN) Explosive J. Am. Chem. Soc. 2009, 131, 7490-7491
24. Mullen, P. A.; Orloff, M. K. Ultraviolet Absorption Spectrum of Pentaerythritol Tetranitrate J. Phys. Chem. 1973, 77, 910-911
25. 4] Following Electronic Excitation J. Chem. Phys. 2011, 135, 154305-1-154305-10
26. Cooper, J. K.; Grant, C. D.; Zhang, J. Z. Experimental and TD-DFT Study of Optical Absorption of Six Explosive Molecules: RDX, HMX, PETN, TNT, TATP, and HMTD J. Phys. Chem. A 2013, 117, 6043-6051
27. Dreger, Z. A.; Gruzdkov, Y. A.; Gupta, Y. M.; Dick, J. J. Shock Wave Induced Decomposition Chemistry of Pentaerythritol Tetranitrate Single Crystals: Time-Resolved Emission Spectroscopy J. Phys. Chem. B 2002, 106, 247-256
28. Aluker, E. D.; Krechetov, A. G.; Mitrofanov, A. Yu.; Nurmukhametov, D. R.; Kuklja, M. M. Laser Initiation of Energetic Materials: Selective Photoinitiation Regime in Pentaerythritol Tetranitrate J. Phys. Chem. C 2011, 115, 6893-6901
29. Aluker, E. D.; Krechetov, A. G.; Mitrofanov, A. Yu.; Zverev, A. S.; Kuklja, M. M. Understanding Limits of the Thermal Mechanism of Laser Initiation of Energetic Materials J. Phys. Chem. C 2012, 116, 24482-24486
30. Conroy, M. W.; Oleynik, I. I.; Zybin, S. V.; White, C. T. First-Principles Investigation of Anisotropic Constitutive Relationships in Pentaerythritol Tetranitrate Phys. Rev. B 2008, 77, 094107-1-094107-8
31. Perger, W. F. Calculation of Band Gaps in Molecular Crystals Using Hybrid Functional Theory Chem. Phys. Lett. 2003, 368, 319-323
32. Kunz, A. B. Ab Initio Investigation of the Crystalline PETN Mater. Res. Soc. Symp. Proc. 1996, 418, 287-292
33. Kuklja, M. M.; Kunz, A. B. Electronic Structure of Molecular Crystals Containing Edge Dislocations J. Appl. Phys. 2001, 89, 4962-4970
34. Chavez, D. E.; Hanson, S. K.; Veauthier, J. M.; Parrish, D. A. Electroactive Explosives: Nitrate Ester-Functionalized 1,2,4,5-Tetrazines Angew. Chem., Int. Ed. 2013, 52, 6876-6879
35. 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 B.01; Gaussian: Wallingford, CT, USA, 2010.
36. Hohenberg, P.; Kohn, W. Inhomogeneous Electron Gas Phys. Rev. 1964, 136, B864-B871
37. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. A 1965, 140, A1133-A1138
38. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
39. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0Model J. Chem. Phys. 1999, 110, 6158-6169
40. Heyd, J.; Scuseria, G. Efficient Hybrid Density Functional Calculations in Solids: Assessment of the Heyd-Scuseria-Ernzerhof Screened Coulomb Hybrid Functional J. Chem. Phys. 2004, 121, 1187-1192
41. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
42. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
43. Bauernschmitt, R.; Ahlrichs, R. Treatment of Electronic Excitations within the Adiabatic Approximation of Time Dependent Density Functional Theory Chem. Phys. Lett. 1996, 256, 454-464
44. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. Molecular Excitation Energies to High-Lying Bound States from Time-Dependent Density-Functional Response Theory: Characterization and Correction of the Time-Dependent Local Density Approximation Ionization Threshold J. Chem. Phys. 1998, 108, 4439-4449
45. Kresse, G.; Futhmuller, J. Efficiency of ab-Initio Total Energy Calculations for Metals and Semiconductors Using a Plane-wave Basis Set Comput. Mater. Sci. 1996, 6, 15-50
46. Kresse, G.; Furthmuller, F. Efficient Iterative Schemes for ab Initio Total-Energy Calculations Using a Plane-wave Basis Set Phys. Rev. B 1996, 54, 11169-11186
47. Kresse, G.; Hafner, J. Ab Initio Molecular Dynamics for Liquid Metals Phys. Rev. B 1993, 47, 558-561
48. Blöchl, P. E. Projector Augmented-Wave Method Phys. Rev. B 1994, 50, 17953-17979
49. Zhu, L.; Ding, C.-F. Temperature Dependence of the Near UV Absorption Spectra and Photolysis Products of Ethyl Nitrate Chem. Phys. Lett. 1997, 265, 177-184
50. He, Sh.; Chen, Zh.; Zhang, X. Photochemical Reactions of Methyl and Ethyl Nitrate: A Dual Role for Alkyl Nitrates in the Nitrogen Cycle Environ. Chem. 2011, 8, 529-542
51. Rebbert, R. E. Primary Processes in the Photolysis of Ethyl Nitrate J. Phys. Chem. 1963, 67, 1923-1925
52. Shishkov, I. F.; Vilkov, L. V.; Bock, C. W.; Hargittai, I. Molecular Structure of Ethyl Nitrate from Gas-Phase Electron Diffraction and ab Initio MO Calculations Chem. Phys. Lett. 1992, 197, 489-494
53. Harris, L. E. The Lower Electronic States of Nitrite and Nitrate Ion, Nitromethane, Nitramide, Nitric Acid, and Nitrate Esters J. Chem. Phys. 1973, 58, 5615-5626
54. Csizmadia, V. M.; Houlden, S. A.; Koves, G. J.; Boggs, J. M.; Csizmadia, I. G. The Stereochemistry and Ultraviolet Spectra of Simple Nitrate Esters J. Org. Chem. 1973, 38, 2281-2287
55. Kaya, K.; Kuwata, K.; Nagakura, S. The Ultraviolet Absorption Spectra of Nitramide and Ethyl Nitrate Bull. Chem. Soc. Jpn. 1964, 37, 1055
56. Roberts, J. M.; Fajer, R. W. UV Absorption Cross Sections of Organic Nitrates of Potential Atmospheric Importance and Estimation of Atmospheric Lifetimes Environ. Sci. Technol. 1989, 23, 945-951
57. Roberts, J. M. The Atmospheric Chemistry of Organic Nitrates Atmos. Environ., Part A 1990, 24, 243-287
58. Talukdar, R. K.; Burkholder, J. B.; Hunter, M.; Gilles, M. K.; Roberts, J. M.; Ravishankara, A. R. Atmospheric Fate of Several Alkyl Nitrates Part 2: UV Absorption Cross-Sections and Photodissociation Quantum Yields J. Chem. Soc., Faraday Trans. 1997, 93, 2797-2805
59. Calvert, J. G.; Pitts, J. N. Photochemistry; Wiley: New York, 1966; p 454.
60. Cady, H. H.; Larson, A. C. Pentaerythritol Tetranitrate II: Its Crystal Structure and Transformation to PETN I; an Algorithm for Refinement of Crystal Structures with Poor Data Acta Crystallogr. 1975, B31, 1864-1869
61. Perdew, J. P.; Levy, M. Physical Content of the Exact Kohn-Sham Orbital Energies: Band Gaps and Derivative Discontinuities Phys. Rev. Lett. 1983, 51, 1884-1887
62. Sham, L. J.; Schluter, M. Density-Functional Theory of the Energy Gap Phys. Rev. Lett. 1983, 51, 1888-1891
63. Perdew, J. P.; Parr, R. G.; Levy, M.; Balduz, J. L. Density-Functional Theory for Fractional Particle Number: Derivative Discontinuities of the Energy Phys. Rev. Lett. 1982, 49, 1691-1694
64. Theory of the Inhomogeneous Electron Gas; Lundqvist, S.; March, N. H., Eds.; Plenum: New York, 1983.
65. Zerilli, F. J.; Hooper, J. P.; Kuklja, M. M. Ab Initio Studies of Crystalline Nitromethane under High Pressure J. Chem. Phys. 2007, 126, 114701-1-114701-8
66. Davydov, A. S. Theory of Molecular Excitons; Plenum Press: New York, 1971; p 313.
67. Siļinš, E. A. Organic Molecular Crystals; Springer-Verlag: Berlin, Heidelberg, 1980; p 392.
68. Hummer, K.; Puschnig, P.; Ambrosch-Draxl, C. Lowest Optical Excitations in Molecular Crystals: Bound Excitons versus Free Electron-Hole Pairs in Anthracene Phys. Rev. Lett. 2004, 92, 147402
69. Hummer, K.; Ambrosch-Draxl, C. Oligoacene Exciton Binding Energies: Their Dependence on Molecular Size Phys. Rev. B 2005, 71, 081202
70. Flicker, W. M.; Mosher, O. A.; Kuppermann, A. Variable Angle Electron-impact Excitation of Nitromethane J. Chem. Phys. 1980, 72, 2788
71. Arenas, J. F.; Otero, J. C.; Peláez, D.; Soto, J. The Ground and Excited State Potential Energy Surfaces of Nitromethane Related to its Dissociation Dynamics after Excitation at 193 nm J. Chem. Phys. 2003, 119, 7814-7823
72. Ungnade, H. E.; Smiley, R. A. Ultraviolet Absorption Spectra of Nitroparaffins, Alkyl Nitrates J. Org. Chem. 1956, 21, 993-996
73. Marinkas, P. L.; Mapes, J. E.; Downs, D. S.; Kemmeyand, P. J.; Forsyth, A. C. Absorption of Cyclic Polynitramines in the Solid and Solvated States Mol. Cryst. Liq. Cryst. 1976, 35, 15
74. Marinkas, P. L. Luminescence of Solid Cyclic Polynitramines J. Lumin. 1977, 15, 57-67
75. Kuklja, M. M.; Stefanovich, E. V.; Kunz, A. B. An Excitonic Mechanism of Detonation Initiation in Explosives J. Chem. Phys. 2000, 112, 3417-3423
76. Guo, Y. Q.; Greenfield, M.; Bhattacharya, A.; Bernstein, E. R. On the Excited Electronic State Dissociation of Nitramine Energetic Materials and Model Systems J. Chem. Phys. 2007, 127, 154301-1-154301-10
77. Bhattacharya, A.; Bernstein, E. R. Nonadiabatic Decomposition of Gas-Phase RDX through Conical Intersections: An ONIOM-CASSCF Study J. Phys. Chem. A 2011, 115, 4135-4147
78. Bhattacharya, A.; Guo, Y. Q.; Bernstein, E. R. Nonadiabatic Reaction of Energetic Molecules Acc. Chem. Res. 2010, 43, 1476-1485
79. Yu, Z.; Bernstein, E. R. On the Decomposition Mechanisms of New Imidazole-Based Energetic Materials J. Phys. Chem. A 2013, 117, 1756-1764