Thin film characterization and vapor sensing properties of a novel perylenediimide material

Sensors and Actuators, B: Chemical

Volumn 160, Issue 1, 2011, Pages 65-71

  Acikbas, Y ^a   Capan, R ^a   Erdogan, M ^a   Yukruk, F ^a  

^a BALIKESIR UNIVERSITY   (Turkey)

Author keywords

Gas sensor; LB thin film; Perylenediimide; Quartz crystal microbalance; Vapor sensor

Indexed keywords

ABSORBANCES; FREQUENCY SHIFT; HIGH QUALITY; ISOPROPYL ALCOHOLS; LANGMUIR-BLODGETT; LINEAR RELATIONSHIPS; MEASUREMENT TECHNIQUES; NOVEL MATERIALS; ORGANIC VAPORS; PERYLENEDIIMIDES; QUARTZ CRYSTAL; ROOM TEMPERATURE; SENSING PROPERTY; THIN FILM FABRICATION PROCESS; THIN-FILM CHARACTERIZATION; VAPOR SENSING; VAPOR SENSOR; VAPOR SENSORS;

AMINO ACIDS; BENZENE; CHEMICAL SENSORS; CHLORINE COMPOUNDS; ETHANOL; LANGMUIR BLODGETT FILMS; QUARTZ; THIN FILM TRANSISTORS; THIN FILMS; TOLUENE; VAPORS;

QUARTZ CRYSTAL MICROBALANCES;

EID: 81155152512     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2011.07.013     Document Type: Article

References (49)

1. H. Zollinger Color Chemistry 2nd ed. 1991 VCH Weinheim
2. W. Herbst, and K. Hunger Industrial Organic Pigments 1993 VCH Weinheim
3. M. Sadrai, L. Hadel, R.R. Sauers, S. Husain, K. Krogh-Jespersen, J.D. Westbrook, and F.R. Bird Lasing action in a family of perylene derivatives: singlet absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calculations J. Phys. Chem. 96 1992 7988 7996
4. S. Icli, S. Demi, B. Dindar, A.O. Doroshenko, and C. Timur Photophysical and photochemical properties of a water-soluble perylene diimide derivative J. Photochem. Photobiol. A 136 2000 15 24
5. S.A. El-Daly, M.K. Awad, S.T. Abdel-Halim, and D.A. Dowidar Photophysical properties and semiempirical calculations of perylene-3,4,9,10-tetracarboxylic tetramethylester (PTME) Spectrochim. Acta Part A 71 2008 1063 1069
6. 2 solar cells with polythiophene hole conductors Sol. Energy Mater. Sol. Cells 88 2005 11 21
7. B.A. Gregg, and R.A. Cormier Doping molecular semiconductors: n-type doping of a liquid crystal perylene diimide J. Am. Chem. Soc. 123 2001 7959 7960
8. A.J. Breeze, A. Salomon, D.S. Ginley, B.A. Gregg, H. Tillmann, and H.H. Horhold Polymer-perylene diimide heterojunction solar cells Appl. Phys. Lett. 81 2002 3085 3087
9. M.H. Kim, M.J. Cho, K.H. Kim, M.H. Hoang, T.W. Lee, J.J.N.S. Kang, J.W. Yu, and D.H. Choi Organic donor-σ-acceptor molecules based on 1,2,4,5-tetrakis((E)-2-(5′-hexyl-2,2′-bithiophen-5-yl)vinyl)benzene and perylene diimide derivative and their application to photovoltaic devices Org. Elect. 10 2009 1429 1441
10. R. Gomez, D. Veldman, R. Blanco, C. Seoane, J.L. Segura, and R.A.J. Janssen Energy and electron transfer in a poly(fluorene-alt-phenylene) bearing perylenediimides as pendant electron acceptor groups Macromolecules 40 2007 2760 2772
11. G.D. Qian, Y. Yang, Z.Y. Wang, C.L. Yang, Z. Yang, and M.Q. Wang Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses Chem. Phys. Lett. 368 2003 555 560
12. R. Gvishi, R. Reisfeld, Z. Brushtein, and Spectroscopy laser action of the red perylimide dye in various solvents Chem. Phys. Lett. 213 1993 338 344
13. Y. Zhang, Z. Xu, L. Cai, G. Lai, H. Qiu, and Y. Shen Highly soluble perylene tetracarboxylic diimides and tetrathiafulvalene-perylene tetracarboxylic diimide-tetrathiafulvalene triads J. Photochem. Photobiol. A 200 2008 334 345
14. R.T. Hayes, M.R. Wasielewski, and D. Gosztola Ultrafast photoswitched charge transmission through the bridge molecule in a donor-bridge-acceptor system J. Am. Chem. Soc. 122 2000 5563 5567
15. W.B. Davis, W.A. Svec, M.A. Ratner, and M.R. Wasielewski Molecular-wire behaviour in p-phenylenevinylene oligomers Nature 396 1998 60 63
16. K. Tomizaki, P. Thamyongkit, R.S. Loewe, and J.S. Lindsey Practical synthesis of perylene-monoimide building blocks that possess features appropriate for use in porphyrin-based light-harvesting arrays Tetrahedron 59 2003 1191 1207
17. K. Tornizaki, R.S. Loewe, C. Kirmaier, J.K. Schwartz, J.L. Retsek, D.F. Bocian, D. Holten, and J.S. Lindsey Synthesis and photophysical properties of light-harvesting arrays comprised of a porphyrin bearing multiple perylene-monoimide accessory pigments J. Org. Chem. 67 2002 6519 6534
18. M.J. Fuller, C.J. Walsh, Y. Zhao, and M.R. Wasielewski Hybrid photorefractive material composed of layered conjugated polymer and dye-doped liquid crystal films Chem. Mater. 14 2002 952 953
19. M.J. Fuller, and M.R. Wasielewski Photorefractivity in nematic liquid crystals using a donor-acceptor dyad with a low-lying excited singlet state for charge generation J. Phys. Chem. B 105 2001 7216 7219
20. B. Ding, W. Zhu, X. Jiang, and Z. Zhang White organic light-emitting diodes based on incomplete energy transfer from perylene to rubrene Solid State Commun. 148 2008 226 229
21. M.A. Angadi, D. Gosztola, and M.R. Wasielewski Organic light emitting diodes using poly(phenylenevinylene) doped with perylenediimide electron acceptors Mater. Sci. Eng. B 63 1999 191 194
22. P. Ranke, I. Bleyl, J. Simmerer, D. Haarer, A. Bacher, and H.W. Schmidt Electroluminescence and electron transport in a perylene dye Appl. Phys. Lett. 71 1997 1332 1334
23. F. Yukruk, A.L. Dogan, H. Canpinar, D. Guc, and E.U. Akkaya Water soluble green perylenediimide (PDI) dyes as potential sensitizers for photodynamic therapy Org. Lett. 7 2005 2885 2887
24. A.L. Briseno, S.C.B. Mannsfeld, C. Reese, J.M. Hancock, Y. Xiong, S.A. Jenekhe, Z. Bao, and Y. Xia Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters Nano Lett. 7 2007 2847 2853
25. L. Zang, Y. Che, and J.S. Moore One-dimensional self-assembly of planar π-conjugated molecules: adaptable building blocks for organic nanodevices Acc. Chem. Res. 41 2008 1596 1608
26. H. Graaf, and D. Schlettwein Influence of gas molecules on the charge carrier mobility in thin films of semiconducting perylene tetracarboxylic imides J. Appl. Phys. 100 2006 126104
27. G.J. Mohr Tailoring the sensitivity and spectral properties of a chromoreactand for the detection of amines and alcohols Anal. Chim. Acta 508 2004 233 237
28. B.P. Jiang, D.S. Guo, and Y. Liu Self-assembly of amphiphilic perylene-cyclodextrin conjugate and vapor sensing for organic amines J. Org. Chem. 75 2010 7258 7264
29. 2) and perylene/bisphthalocyanine as new structures for gas sensing Sens. Actuators B 145 2010 501 506
30. Y. Liu, K.R. Wang, D.S. Guo, and B.P. Jiang Supramolecular assembly of perylene bisimide with β-cyclodextrin grafts as a solid-state fluorescence sensor for vapor detection Adv. Funct. Mater. 19 2009 2230 2235
31. F.L. Castro, J.G. Santos, G.J.T. Fernandes, A.S. Araújo, V.J. Fernandes Jr., M.J. Politi, and S. Brochsztain Solid state fluorescence of a 3,4,9,10-perylenetetracarboxylic diimide derivative encapsulated in the pores of mesoporous silica MCM-41 Micropor. Mesopor. Mater. 102 2007 258 264
32. D.Y. Sasaki, S. Singh, J.D. Cox, and P.I. Pohl Fluorescence detection of nitrogen dioxide with perylene/PMMA thin films Sens. Actuators B 72 2001 51 55
33. T. Oekermann, D. Schlettwein, and N.I. Jaeger Charge transfer and recombination kinetics at electrodes of molecular semiconductors investigated by intensity modulated photocurrent spectroscopy J. Phys. Chem. B 105 2001 9524 9532
34. Y. Che, X. Yang, S. Loser, and L. Zang Expedient vapor probing of organic amines using fluorescent nanofibers fabricated from an n-type organic semiconductor Nano Lett. 8 2008 2219 2223
35. S.H. Han, K.J. Lee, S.H. Lee, and J. Jang N-type organic thin-film transistor using N,N′-dioctyl-3,4,9,10-perylene tetracarboxylic diimides grown by organic vapor deposition J. Non-Cryst. Solids 354 2008 2870 2874
36. E. Wolarz, E. Mykowska, T. Martyński, and R. Stolarski Electronic absorption and fluorescence of new tetrafluoro-pentenyl-perylene in isotropic solvents, liquid crystal layers, and LB films J. Mol. Struct. 929 2009 79 84
37. Y. Chen, Y. Kong, Y. Wang, P. Ma, M. Bao, and X. Li Supramolecular self-assembly study of a flexible perylenetetracarboxylic diimide dimer in Langmuir and Langmuir-Blodgett films J. Coll. Interface Sci. 330 2009 421 427
38. M. Furuki, and L. Pu Gas detection by a multi-hybrid sensor with dye Langmuir-Blodgett films deposited on a quartz oscillator Mol. Cryst. Liq. Cryst. 227 1993 325 337
39. C.J.L. Constantino, P.A. Antunes, E.C. Venancio, N. Consolin, F.J. Fonseca, L.H.C. Mattoso, R.F. Aroca, O.N. Oliveira, and A. Riul Nanostructured films of perylene derivatives: high performance materials for taste sensor applications Sens. Lett. 2 2004 95 101
40. A. Menikh, and A. Bouraoui Spectroscopic and electrochemical studies of N,N′-bis(decamethylcarboxylic)-3,4,9,10-perylene-bis(dicarboxyimide) J. Mol. Struct. 403 1997 189 197
41. M.M. Shi, H.Z. Chen, J.Z. Sun, J. Ye, and M. Wang Effect of fluorination on aggregate structure of perylene dimide Chin. Chem. Lett. 15 2004 575 578
42. Y. Zhao, and M.R. Wasielewski 3,4,9,10-Perylenebis(dicarboximide) chromophores that function as both electron donors and acceptors Tetrahedron Lett. 40 1999 7047 7050
43. F. Yukruk, and E.U. Akkaya Modulation of internal charge transfer (ICT) in a bay region hydroxylated perylenediimide (PDI) chromophore: a chromogenic chemosensor for pH Tetrahedron Lett. 46 2005 5931 5933
44. L.Y. Yang, M.M. Shi, M. Wang, and H.Z. Chen Self-assembled helical nanostructures from an asymmetrical perylene diimide Chin. Chem. Lett. 19 2008 1260 1263
45. R. Aroca, and C.J.L. Constantino Surface-enhanced Raman scattering: imaging and mapping of Langmuir-Blodgett monolayers physically adsorbed onto silver island films Langmuir 16 2000 5425 5429
46. P.A. Antunes, C.J.L. Constantino, R.F. Aroca, and J. Duff Langmuir and Langmuir-Blodgett films of perylene tetracarboxylic derivatives with varying alkyl chain length: film packing and surface-enhanced fluorescence studies Langmuir 17 2001 2958 2964
47. W.S. Shin, H.H. Jeong, M.K. Kim, S.H. Jin, M.R. Kim, J.K. Lee, J.W. Lee, and Y.S. Gal Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application J. Mater. Chem. 16 2006 384 390
48. P. Sun, Y. Jiang, G. Xie, J. Yu, X. Du, and J. Hu Synthesis and sensitive properties of poly-(bistriethylphosphine)-platinum-diethynylbenzene for organic vapor detection J. Appl. Polym. Sci. 116 2010 562 567
49. L.G. Xu, X. Hu, Y.T. Lim, and V.S. Subramanian Organic vapor adsorption behavior of poly(3-butoxythiophene) LB films on quartz crystal microbalance Thin Solid Films 417 2002 90 94