A Surface Chemical Reaction in Organic-Inorganic Materials Using a New Chemical Evaporation System

Chemistry of Materials

Volumn 27, Issue 13, 2015, Pages 4546-4551

  Kim, Seong Jun ^a,b   Myung, Sung ^a   Song, Wooseok ^a   Min, Bok Ki ^a   Hong, Seong Jin ^a   Chung, Myungwoo ^c   Kim, Hyunjung ^c   Kong, Ki Jeong ^a   Lim, Jongsun ^a   Chung, Taek Mo ^a   An, Ki Seok ^a,b  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b University of Science and Technology (UST)   (South Korea)

^c Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; DEPOSITION; EVAPORATION; FILM GROWTH; METALS; SEMICONDUCTOR GROWTH; SURFACE REACTIONS; THERMAL EVAPORATION; VAPOR DEPOSITION; X RAY PHOTOELECTRON SPECTROSCOPY;

CHEMICAL EQUATIONS; EVAPORATION SYSTEMS; HYBRID DEPOSITION SYSTEMS; ORGANIC-INORGANIC HYBRID; ORGANIC-INORGANIC MATERIALS; SURFACE CHEMICAL REACTIONS; THEORETICAL SIMULATION; ZINC TETRAPHENYLPORPHYRIN;

THIN FILMS;

EID: 84937249984     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.5b00377     Document Type: Article

References (39)

1. Biesaga, M.; Pyrzyńska, K.; Trojanowicz, M. Porphyrins in Analytical Chemistry. A Review Talanta 2000, 51, 209-224
2. Gamboa, M.; Campos, M.; Alfonso Torres, L. Study of the Stability of 5,10,15,20-Tetraphenylporphine (TPP) and Metallo-Porphyrins NiTPP, CoTPP, CuTPP, and ZnTPP by Differential Scanning Calorimetry and Thermogravimetry J. Chem. Thermodyn. 2010, 42, 666-674
3. Cuesta, L.; Sessler, J. L. π-Metal Complexes of Tetrapyrrolic Systems. A Novel Coordination Mode in "Porphyrin-like" Chemistry Chem. Soc. Rev. 2009, 38, 2716-2729
4. Balanay, M. P.; Hee Kim, D. Structures and Excitation Energies of Zn-Tetraarylporphyrin Analogues: A Theoretical Study THEOCHEM 2009, 910, 20-26
5. Auwa¨rter, W.; Weber-Bargioni, A.; Brink, S.; Riemann, A.; Schiffrin, A.; Ruben, M.; Barth, J. V. Controlled Metalation of Self-Assembled Porphyrin Nanoarrays in Two Dimensions ChemPhysChem 2007, 8, 250-254
6. 70 Donor-Acceptor Complex For Solar Cells Surf. Sci. 2006, 600, 4018-4023
7. 4- in Aqueous Media Chem. Phys. Lett. 2011, 501, 278-282
8. Campbell, W. M.; Jolley, K. W.; Wagner, P.; Wagner, K.; Walsh, P. J.; Gordon, K. C.; Schmidt-Mende, L.; Nazeeruddin, M. K.; Wang, Q.; Gra1tzel, M.; Officer, D. L. Highly Efficient Porphyrin Sensitizers for Dye-Sensitized Solar Cells J. Phys. Chem. C 2007, 111, 11760-11762
9. 2 Films J. Phys. Chem. B 2005, 109, 15397-15409
10. Che, C. M.; Xiang, H. F.; Chui, S. S.-Y.; Xu, Z. X.; Roy, V. A. L.; Yan, J. J.; Fu, W. F.; Lai, P. T.; Williams, I. D. A High-Performance Organic Field-Effect Transistor Based on Platinum(II) Porphyrin: Peripheral Substituents on Porphyrin Ligand Significantly Affect Film Structure and Charge Mobility Chem.-Asian J. 2008, 3, 1092-1103
11. Hoang, M. H.; Kim, Y.; Kim, S. J.; Choi, D. H.; Lee, S. J. High-Performance Single-Crystal-Based Organic Field-Effect Transistors from π-Extended Porphyrin Derivatives Chem.-Eur. J. 2011, 17, 7772-7776
12. Dini, F.; Magna, G.; Martinelli, E.; Paolesse, R.; Filippini, D.; Lundström, I.; Natale, C. D. Gas Sensitivity of Blends of Metalloporphyrins and Colorimetric Acid-Base Indicators Proc. Eng. 2011, 25, 1413-1416
13. Sayyad, M. H.; Saleem, M.; Karimov, K. S.; Yaseen, M.; Ali, M.; Cheong, K. Y.; Mohd Noor, A. F. Synthesis of Zn(II) 5,10,15,20-Tetrakis(4′-isopropylphenyl)porphyrin and Its Use As a Thin Film Sensor Appl. Phys. A: Mater. Sci. Process. 2010, 98, 103-109
14. Ahmad, Z.; Sayyad, M. H.; Yaseen, M.; Aw, K. C.; M-Tahir, M.; Ali, M. Potential of 5,10,15,20-Tetrakis(3′,5′-di-tertbutylphenyl)porphyrinatocopper(II) for a multifunctional sensor Sens. Actuators, B 2011, 155, 81-85
15. Buchner, F.; Flechtner, K.; Bai, Y.; Zillner, E.; Kellner, I.; Steinrück, H. P.; Marbach, H.; Gottfried, J. M. Coordination of Iron Atoms by Tetraphenylporphyrin Monolayers and Multilayers on Ag(111) and Formation of Iron-Tetraphenylporphyrin J. Phys. Chem. C 2008, 112, 15458-15465
16. Gottfried, J. M.; Flechtner, K.; Kretschmann, A.; Lukasczyk, T.; Steinrück, H. P. Direct Synthesis of a Metalloporphyrin Complex on a Surface J. Am. Chem. Soc. 2006, 128, 5644-5645
17. González-Moreno, R.; Sánchez-Sánchez, C.; Trelka, M.; Otero, R.; Cossaro, A.; Verdini, A.; Floreano, L.; Ruiz-Bermejo, M.; García-Lekue, A.; ángel Martín-Gago, J.; Rogero, C. Following the Metalation Process of Protoporphyrin IX with Metal Substrate Atoms at Room Temperature J. Phys. Chem. C 2011, 115, 6849-6854
18. Kretschmann, A.; Walz, M. M.; Flechtner, K.; Steinrück, H. P.; Gottfried, J. M. Tetraphenylporphyrin Picks up Zinc Atoms from a Silver Surface Chem. Commun. 2007, 568-570
19. Shubina, T. E.; Marbach, H.; Flechtner, K.; Kretschmann, A.; Jux, N.; Buchner, F.; Steinrück, H. P.; Clark, T.; Gottfried, J. M. Principle and Mechanism of Direct Porphyrin Metalation: Joint Experimental and Theoretical Investigation J. Am. Chem. Soc. 2007, 129, 9476-9483
20. Diller, K.; Klappenberger, F.; Marschall, M.; Hermann, K.; Nefedov, A.; Wöll, Ch.; Barth, J. V. Self-Metalation of 2 H -Tetraphenylporphyrin on Cu(111): An X-ray Spectroscopy Study J. Chem. Phys. 2012, 136, 014705
21. 2(110) sSurface Chem. Commun. 2014, 50, 8291-8294
22. Zhang, L.; Patil, A. J.; Li, L.; Schierhorn, A.; Mann, S.; Gösele, U.; Knez, M. Chemical Infiltration during Atomic Layer Deposition: Metalation of Porphyrins as Model Substrates Angew. Chem., Int. Ed. 2009, 48, 4982-4985
23. George, S. M. Atomic Layer Deposition: An Overview Chem. Rev. 2010, 110, 111-131
24. Loscutoff, P. W.; Lee, H. B. R.; Bent, S. F. Deposition of Ultrathin Polythiourea Films by Molecular Layer Deposition Chem. Mater. 2010, 22, 5563-5569
25. Yoon, K. H.; Han, K. S.; Sung, M. M. Fabrication of a New Type of Organic-Inorganic Hybrid Superlattice Films Combined with Titanium Oxide and Polydiacetylene Nanoscale Res. Lett. 2012, 7, 71
26. Papageorgiou, A. C.; Fischer, S.; Oh, S. C.; Saʇlam; Reichert, J.; Wiengarten, A.; Seufert, K.; Vijayaraghavan, S.; Ecija, D.; Auwa¨rter, W.; Allegretti, F.; Acres, R. G.; Prince, K. C.; Diller, K.; Klappenberger, F.; Barth, J. V. Self-Terminating Protocol for an Interfacial Complexation Reaction in Vacuo by Metal-Organic Chemical Vapor Deposition ACS Nano 2013, 7, 4520-4526
27. 2 Matrixes J. Phys. Chem. B 2002, 106, 1853-1861
28. Furuta, H.; Morimoto, T.; Osuka, A. Syntheses, Structures, and Crystal Packing of N-Confused 5,20-Diphenylporphyrin and Ag(III) Complex Org. Lett. 2003, 5, 1427-1430
29. Summerville, D. A.; Cohen, I. A.; Hatano, K.; Scheidt, W. R. Preparation and Physical and Stereochemical Characterization of the Tricyanomethanide Salt of 5,10,15,20-Tetraphenylporphinatoiron(III). A Six-Coordinate Intermediate-Spin Complex Inorg. Chem. 1978, 17, 2906-2910
30. Saini, G. S. S. Resonance Raman Study of Free-Base Tetraphenylporphine and Its Dication Spectrochim. Acta Part A 2006, 64, 981-986
31. Akins, D. L.; Guo, C.; Zhu, H.-R. Near-Infrared-Excited FT-Raman Spectra of Covalently Linked Porphyrin-Nitrobenzene Compounds J. Phys. Chem. 1993, 97, 3974-3977
32. Reed, R. A.; Purrello, R.; Prendergast, K.; Spiro, T. C. Resonance Raman Characterization of the Radical Anion and Triplet States of Zinc Tetraphenylporphine J.. Phys. Chem. 1991, 95, 9720-9727
33. Scha¨ferling, M.; Baüerle, P. Porphyrin-Functionalized Oligo- and Polythiophenes J. Mater. Chem. 2004, 14, 1132-1141
34. Retsek, J. L.; Medforth, C. J.; Nurco, D. J.; Gentemann, S.; Chirvony, V. S.; Smith, K. M.; Holten, D. Conformational and Electronic Effects of Phenyl-Ring Fluorination on the Photophysical Properties of Nonplanar Dodecaarylporphyrins J. Phys. Chem. B 2001, 105, 6396-6411
35. Ditze, S.; Stark, M.; Drost, M.; Buchner, F.; Steinrück, H. P.; Marbach, H. Activation Energy for the Self-Metalation Reaction of 2 H -Tetraphenylporphyrin on Cu(111) Angew. Chem., Int. Ed. 2012, 51, 10898-10901
36. Delley, B. An All-Electron Numerical Method for Solving the Local Density Functional for Polyatomic Molecules J. Chem. Phys. 1990, 92, 508-517
37. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
38. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132, 154104
39. Govind, N.; Petersen, M.; Fitzgerald, G.; King-Smith; An-dzelm, D. J. A Generalized Synchronous Transit Method for Transition State Location Comput. Mater. Sci. 2003, 28, 250-258