New organic-inorganic hybrid materials based on perylene diimide-polyhedral oligomeric silsesquioxane dyes with reduced quenching of the emission in the solid state

Dyes and Pigments

Volumn 96, Issue 3, 2013, Pages 748-755

  Lucenti, Elena ^a,b   Botta, Chiara ^a   Cariati, Elena ^b,c   Righetto, Stefania ^b,c   Scarpellini, Michele ^b,c   Tordin, Elisa ^b,c   Ugo, Renato ^b,c  

^a CNR   (Italy)

^b INSTM (Material Science and Technology National Consortium)   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

extended polycyclic aromatic rings; Aggregation caused quenching; Hybrid materials; Perylene tetracarboxylic acid diimide; Photoluminescence; Polyhedral oligomeric silsesquioxanes

Indexed keywords

CONDENSED PHASE; DIIMIDE; ELECTRONIC ABSORPTION SPECTRA; EMISSION FEATURES; FLUORESCENCE QUANTUM YIELD; HIGH EMISSION INTENSITY; HIGH-TECH APPLICATIONS; LIGHT EMITTING MATERIALS; LUMINESCENT MATERIAL; OPTICAL INVESTIGATION; ORGANIC-INORGANIC HYBRID MATERIALS; PERYLENE TETRACARBOXYLIC; PERYLENEDIIMIDES; PERYLENES; POLYCYCLIC AROMATICS; POLYHEDRAL OLIGOMERIC SILSESQUIOXANES; QUENCHING PROCESS; SILSESQUIOXANES; SPIN-COATED FILMS;

HYBRID MATERIALS; ORGANIC COATINGS; PHOTOLUMINESCENCE; POLYCYCLIC AROMATIC HYDROCARBONS; QUANTUM YIELD; QUENCHING;

OLIGOMERS;

EID: 84870940518     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.11.015     Document Type: Article

References (84)

1. M. Shimizu, and T. Hiyama Organic fluorophores exhibiting highly efficient photoluminescence in the solid state Chemistry-An Asian Journal 5 7 2010 1516 1531
2. C. Burgdorff, H.G. Loehmannsroeben, and R. Reisfeld A perylene dye in sol-gel matrixes: photophysical properties of N,N′-bis(2,5-di-tert- butylphenyl)-3,4:9,10-perylenebis(dicarboximide) in glasses and thin films Chemical Physics Letters 197 4, 5 1992 358 363
3. C. Huang, S. Barlow, and S.R. Marder Perylene-3,4,9,10-tetracarboxylic acid diimides: synthesis, physical properties, and use in organic electronics Journal of Organic Chemistry 76 8 2011 2386 2407
4. J. Mizuguchi Electronic characterization of N, N′-bis(2- phenylethyl)perylene-3,4:9, 10-bis(dicarboximide) and its application to optical disks Journal of Applied Physics 84 8 1998 4479 4486
5. J. Mizuguchi, and K. Tojo Electronic structure of perylene pigments as viewed from the crystal structure and excitonic interactions Journal of Physical Chemistry B 106 4 2002 767 772
6. S. Yagai, T. Seki, T. Karatsu, A. Kitamura, and F. Würthner Transformation from H- to J-aggregated perylene bisimide dyes by complexation with cyanurates Angewandte Chemie International Edition 47 18 2008 3367 3371
7. H. Langhals Control of the interactions in multichromophores: novel concepts. Perylene bis-imides as components for larger functional units Helvetica Chimica Acta 88 6 2005 1309 1343
8. M.J. Ahrens, M.J. Fuller, and M.R. Wasielewski Cyanated perylene-3,4-dicarboximides and perylene-3,4:9,10-bis(dicarboximide): facile chromophoric oxidants for organic photonics and electronics Chemistry of Materials 15 14 2003 2684 2686
9. H.Z. Chen, M.M. Ling, X. Mo, M.M. Shi, M. Wang, and Z. Bao Air stable n-channel organic semiconductors for thin film transistors based on fluorinated derivatives of perylene diimides Chemistry of Materials 19 4 2007 816 824
10. A.J. Jiménez, F. Spänig, M.S. Rodríguez-Morgade, K. Ohkubo, S. Fukuzumi, and D.M. Guldi A tightly coupled bis(zinc(II) phthalocyanine)-perylenediimide ensemble to yield long-lived radical ion pair states Organic Letters 9 13 2007 2481 2484
11. B.A. Jones, M.J. Ahrens, M.-H. Yoon, A. Facchetti, T.J. Marks, and M.R. Wasielewski Electron transport: high-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides) Angewandte Chemie International Edition 43 46 2004 6363 6366
12. B.J. Jung, N.J. Tremblay, M.-L. Yeh, and H.E. Katz Molecular design and synthetic approaches to electron-transporting organic transistor semiconductors Chemistry of Materials 23 3 2011 568 582
13. S.M. Lindner, N. Kaufmann, and M. Thelakkat Nanostructured semiconductor block copolymers: π-π stacking, optical and electrochemical properties Organic Electronics 8 1 2007 69 75
14. X. Zhan, A. Facchetti, S. Barlow, T.J. Marks, M.A. Ratner, and M.R. Wasielewski Rylene and related diimides for organic electronics Advanced Materials 23 2 2011 268 284
15. X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, and S. Barlow A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells Journal of American Chemical Society 129 23 2007 7246 7247
16. R. Gvishi, R. Reisfeld, and Z. Burshtein Spectroscopy and laser action of the "red perylimide dye" in various solvents Chemical Physics Letters 213 3, 4 1993 338 344
17. K.Y. Law Organic photoconductive materials: recent trends and developments Chemical Reviews 93 1 1993 449 486
18. W.E. Ford, and P.V. Kamat Photochemistry of 3,4,9,10- perylenetetracarboxylic dianhydride dyes. 3. Singlet and triplet excited-state properties of the bis(2,5-di-tert-butylphenyl)imide derivative Journal of Physical Chemistry 91 25 1987 6373 6380
19. M. Sadrai, and G.R. Bird A new laser dye with potential for high stability and a broad band of lasing action: perylene-3,4,9,10-tetracarboxylic acid-bis-N,N′-(2′,6′-xylidyl)diimide Optics Communications 51 1 1984 62 64
20. C. Li, and H. Wonneberger Perylene imides for organic photovoltaics: yesterday, today, and tomorrow Advanced Materials 24 5 2012 613 636
21. J.E. Anthony Small-molecule, nonfullerene acceptors for polymer bulk heterojunction organic photovoltaics Chemistry of Materials 23 3 2011 583 590
22. Y. Avlasevich, C. Li, and K. Muellen Synthesis and applications of core-enlarged perylene dyes Journal of Materials Chemistry 20 19 2010 3814 3826
23. L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R.H. Friend, and J.D. MacKenzie Self-organized discotic liquid crystals for high-efficiency organic photovoltaics Science 293 5532 2001 1119 1122
24. Z. Tan, E. Zhou, X. Zhan, X. Wang, Y. Li, and S. Barlow Efficient all-polymer solar cells based on blend of tris(thienylenevinylene)-substituted polythiophene and poly[perylene diimide-alt-bis(dithienothiophene)] Applied Physics Letters 93 7 2008 073309/1e073309/3
25. K.D. Belfield, M.V. Bondar, F.E. Hernandez, and O.V. Przhonska Photophysical characterization, two-photon absorption and optical power limiting of two fluorenylperylene diimides Journal of Physical Chemistry C 112 14 2008 5618 5622
26. Z. An, S.A. Odom, R.F. Kelley, C. Huang, X. Zhang, and S. Barlow Synthesis and photophysical properties of donor- and acceptor-substituted 1,7-bis(arylalkynyl)perylene-3,4:9,10-bis(dicarboximide)s Journal of Physical Chemistry A 113 19 2009 5585 5593
27. S. Fukuzumi, K. Ohkubo, J. Ortiz, A.M. Gutierrez, F. Fernandez-Lazaro, and A. Sastre-Santos Formation of a long-lived charge-separated state of a zinc phthalocyanine-perylenediimide dyad by complexation with magnesium ion Chemical Communications 30 2005 3814 3816
28. M.P. O'Neil, M.P. Niemczyk, W.A. Svec, D. Gosztola, G.L. Gaines, and M.R. Wasielewski Picosecond optical switching based on biphotonic excitation of an electron donor-acceptor-donor molecule Science 257 5066 1992 63 65
29. S. Prathapan, S.I. Yang, J. Seth, M.A. Miller, D.F. Bocian, and D. Holten Synthesis and excited-state photodynamics of perylene-porphyrin dyads. 1. Parallel energy and charge transfer via a diphenylethyne linker Journal of Physical Chemistry B 105 34 2001 8237 8248
30. J.M. Serin, D.W. Brousmiche, and J.M.J. Fréchet Cascade energy transfer in a conformationally mobile multichromophoric dendrimer Chemical Communications 22 2002 2605 2607
31. S. Shoaee, Z. An, X. Zhang, S. Barlow, S.R. Marder, and W. Duffy Charge photogeneration in polythiophene-perylene diimide blend films Chemical Communications 36 2009 5445 5447
32. F. Würthner Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures Chemical Communications 14 2004 1564 1579
33. H. Langhals Cyclic carboxylic imide structures as structure elements of high stability. Novel developments in perylene dye chemistry Heterocycles 40 1 1995 477 500
34. H. Langhals, R. Ismael, and O. Yuruk Persistent fluorescence of perylene dyes by steric inhibition of aggregation Tetrahedron 56 30 2000 5435 5441
35. H. Langhals, O. Krotz, K. Polborn, and P. Mayer A novel fluorescent dye with strong, anisotropic solid-state fluorescence, small Stokes shift, and high photostability Angewandte Chemie International Edition 44 16 2005 2427 2428
36. F. Würthner, T.E. Kaiser, and C.R. Saha-Möller J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials Angewandte Chemie International Edition England 50 15 2011 3376 3410
37. S. Nakazono, S. Easwaramoorthi, D. Kim, H. Shinokubo, and A. Osuka Synthesis of arylated perylene bisimides through C-H bond cleavage under ruthenium catalysis Organic Letters 11 23 2009 5426 5429
38. S. Nakazono, Y. Imazaki, H. Yoo, J. Yang, T. Sasamori, and N. Tokitoh Regioselective Ru-catalyzed direct 2,5,8,11-alkylation of perylene bisimides Chemistry-A European Journal 15 31 2009 7530 7533 S/1-S/25
39. R.H. Baney, M. Itoh, A. Sakakibara, and T. Suzuki Silsesquioxanes Chemical Reviews 95 5 1995 1409 1430
40. D.B. Cordes, P.D. Lickiss, and F. Rataboul Recent developments in the chemistry of cubic polyhedral oligosilsesquioxanes Chemical Reviews 110 4 2010 2081 2173
41. F.J. Feher, and T.A. Budzichowski Silasesquioxanes as ligands in inorganic and organometallic chemistry Polyhedron 14 22 1995 3239 3253
42. P.G. Harrison Silicate cages: precursors to new materials Journal of Organometallic Chemistry 542 2 1997 141
43. R.M. Laine, and M.F. Roll Polyhedral phenylsilsesquioxanes Macromolecules 44 5 2011 1073 1109
44. S.H. Phillips, T.S. Haddad, and S.J. Tomczak Developments in nanoscience: polyhedral oligomeric silsesquioxane (POSS)-polymers Current Opinion in Solid State & Materials Science 8 1 2004 21 29
45. H. Fong, S.H. Dickens, and G.M. Flaim Evaluation of dental restorative composites containing polyhedral oligomeric silsesquioxane methacrylate Dental Materials 21 6 2005 520 529
46. F. Gao, Y. Tong, S.R. Schricker, and B.M. Culbertson Evaluation of neat resins based on methacrylates modified with methacryl-POSS, as potential organic-inorganic hybrids for formulating dental restoratives Polymers for Advanced Technologies 12 6 2001 355 360
47. R.Y. Kannan, H.J. Salacinski, P.E. Butler, and A.M. Seifalian Polyhedral oligomeric silsesquioxane nanocomposites: the next generation material for biomedical applications Accounts of Chemical Research 38 11 2005 879 884
48. C.-M. Leu, Y.-T. Chang, and K.-H. Wei Polyimide-side-chain tethered polyhedral oligomeric silsesquioxane nanocomposites for low-dielectric film applications Chemistry of Materials 15 19 2003 3721 3727
49. E. Tegou, V. Bellas, E. Gogolides, P. Argitis, D. Eon, and G. Cartry Polyhedral oligomeric silsesquioxane (POSS) based resists: material design challenges and lithographic evaluation at 157 nm Chemistry of Materials 16 13 2004 2567 2577
50. H.C.L. Abbenhuis Advances in homogeneous and heterogeneous catalysis with metal-containing silsesquioxanes Chemistry-A European Journal 6 1 2000 25 32
51. F. Carniato, C. Bisio, E. Boccaleri, M. Guidotti, E. Gavrilova, and L. Marchese Titanosilsesquioxane anchored on mesoporous silicas: a novel approach for the preparation of heterogeneous catalysts for selective oxidations Chemistry-A European Journal 14 27 2008 8098 8101
52. R. Duchateau Incompletely condensed silsesquioxanes: versatile tools in developing silica-supported olefin polymerization catalysts Chemical Reviews 102 10 2002 3525 3542
53. R. Duchateau, H.C.L. Abbenhuis, R.A. van Santen, A. Meetsma, S.K.H. Thiele, and M.F.H. van Tol Ethylene polymerization with dimeric zirconium and hafnium silsesquioxane complexes Organometallics 17 26 1998 5663 5673
54. F.J. Feher, and R.L. Blanski Olefin polymerization by vanadium-containing silsesquioxanes: synthesis of a dialkyl-oxo-vanadium(V) complex that initiates ethylene polymerization Journal of American Chemical Society 114 14 1992 5886 5887
55. 4] Organometallics 10 7 1991 2526 2528
56. F.J. Feher, D.A. Newman, and J.F. Walzer Silsesquioxanes as models for silica surfaces Journal of American Chemical Society 111 5 1989 1741 1748
57. F.J. Feher, D. Soulivong, A.G. Eklund, and K.D. Wyndham Cross-metathesis of alkenes with vinyl-substituted silsesquioxanes and spherosilicates: a new method for synthesizing highly-functionalized Si/O frameworks Chemical Communications 13 1997 1185 1186
58. R.W.J.M. Hanssen, R.A. van Santen, and H.C.L. Abbenhuis The dynamic status quo of polyhedral silsesquioxane coordination chemistry European Journal of Inorganic Chemistry 4 2004 675 683
59. P.P. Pescarmona, J.C. Van der Waal, I.E. Maxwell, and T. Maschmeyer A new, efficient route to titanium-silsesquioxane epoxidation catalysts developed by using high-speed experimentation techniques Angewandte Chemie International Edition 40 4 2001 740 743
60. E.A. Quadrelli Molecular insight for silica-supported organometallic chemistry through transition metal silsesquioxanes J.-M. Basset, R. Psaro, D. Roberto, R. Ugo, Modern surface organometallic chemistry 2009 Wiley-VCH Weinheim, Germany 557 598
61. J.R. Severn, R. Duchateau, R.A. van Santen, D.D. Ellis, and A.L. Spek Homogeneous models for chemically tethered silica-supported olefin polymerization catalysts Organometallics 21 1 2002 4 6
62. A.J. Ward, A.F. Masters, and T. Maschmeyer Transition metal single site catalysts-from homogeneous to immobilized systems J.-M. Basset, R. Psaro, D. Roberto, R. Ugo, Modern surface organometallic chemistry 2009 Wiley-VCH Weinheim, Germany 167 237
63. S. Xiao, M. Nguyen, X. Gong, Y. Cao, H. Wu, and D. Moses Stabilization of semiconducting polymers with silsesquioxane Advanced Functional Materials 13 1 2003 25 29
64. K.L. Chan, P. Sonar, and A. Sellinger Cubic silsesquioxanes for use in solution processable organic light emitting diodes (OLED) Journal of Materials Chemistry 19 48 2009 9103 9120
65. J.D. Froehlich, R. Young, T. Nakamura, Y. Ohmori, S. Li, and A. Mochizuki Synthesis of multi-functional POSS emitters for OLED applications Chemistry of Materials 19 20 2007 4991 4997
66. R.M. Laine, S. Sulaiman, C. Brick, M. Roll, R. Tamaki, and M.Z. Asuncion Synthesis and photophysical properties of Stilbeneoctasilsesquioxanes. Emission behavior coupled with theoretical modeling studies suggest a 3-D excited state involving the silica core Journal of American Chemical Society 132 11 2010 3708 3722
67. M.Y. Lo, C. Zhen, M. Lauters, G.E. Jabbour, and A. Sellinger Organic-inorganic hybrids based on pyrene functionalized octavinylsilsesquioxane cores for application in OLEDs Journal of American Chemical Society 129 18 2007 5808 5809
68. X. Yang, J.D. Froehlich, H.S. Chae, S. Li, A. Mochizuki, and G.E. Jabbour Efficient light-emitting devices based on phosphorescent polyhedral oligomeric silsesquioxane materials Advanced Functional Materials 19 16 2009 2623 2629
69. C.-H. Chou, S.-L. Hsu, K. Dinakaran, M.-Y. Chiu, and K.-H. Wei Synthesis and characterization of luminescent polyfluorenes incorporating side-chain-tethered polyhedral oligomeric silsesquioxane units Macromolecules 38 3 2005 745 751
70. D. Clarke, S. Mathew, J. Matisons, G. Simon, and B.W. Skelton Synthesis and characterization of a range of POSS imides Dyes and Pigments 92 1 2011 659 667
71. F. Du, J. Tian, H. Wang, B. Liu, B. Jin, and R. Bai Synthesis and luminescence of POSS-containing perylene bisimide-bridged amphiphilic polymers Macromolecules 45 7 2012 3086 3093
72. X. Ren, B. Sun, C.-C. Tsai, Y. Tu, S. Leng, and K. Li Synthesis, self-assembly, and crystal structure of a shape-persistent polyhedral- oligosilsesquioxane-nanoparticle-tethered perylene diimide Journal of Physical Chemistry B 114 14 2010 4802 4810
73. Jeganathan SG, Bramer D, Kote R, Maladkar GJ. Ciba specialty chemicals Corp., USA. Novel polyhedral oligomeric silsesquioxane based fluorescent colorants, U.S. Patent 2008/0029739; 2008.
74. F.J. Feher, R. Terroba, and J.W. Ziller A new route to incompletely-condensed silsesquioxanes: base-mediated cleavage of polyhedral oligosilsesquioxanes Chemical Communications 22 1999 2309 2310
75. E.G. Shockey, A.G. Bolf, P.F. Jones, J.J. Schwab, K.P. Chaffee, and T.S. Haddad Functionalized polyhedral oligosilsesquioxane (POSS) macromers: new graftable POSS hydride, POSS α-olefin, POSS epoxy, and POSS chlorosilane macromers and POSS-siloxane triblocks Applied Organometallic Chemistry 13 4 1999 311 327
76. H. Langhals, and A.J. Esterbauer Fluorescent silica nanoparticles by silylation Chemistry-A European Journal 15 19 2009 4793 4796
77. H. Langhals, A.J. Esterbauer, A. Walter, E. Riedle, and I. Pugliesi Foerster resonant energy transfer in orthogonally arranged chromophores Journal of American Chemical Society 132 47 2010 16777 16782
78. S. Demmig, and H. Langhals Very soluble and photostable perylene fluorescent dyes Chemische Berichte 121 2 1988 225 230
79. N. Soh, T. Ariyoshi, T. Fukaminato, H. Nakajima, K. Nakano, and T. Imato Swallow-tailed perylene derivative: a new tool for fluorescent imaging of lipid hydroperoxides Organic & Biomolecular Chemistry 5 23 2007 3762 3768
80. J. Moreau, U. Giovanella, J.-P. Bombenger, W. Porzio, V. Vohra, and L. Spadacini Highly emissive nanostructured thin films of organic host-guests for energy conversion ChemPhysChem 10 4 2009 647 653
81. 3 as ligands Accounts of Chemical Research 41 11 2008 1555 1564
82. A.F. Littke, and G.C. Fu A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions Journal of American Chemical Society 123 29 2001 6989 7000
83. D.K. Mohamad, A. Fischereder, H.-N. Yi, A.J. Cadby, D.G. Lidzey, and A. Iraqi A novel 2,7-linked carbazole based "double cable" polymer with pendant perylene diimide functional groups: preparation, spectroscopy and photovoltaic properties Journal of Materials Chemistry 21 3 2011 851 862
84. H. Langhals, J. Karolin, and L.B.A. Johansson Spectroscopic properties of new and convenient standards for measuring fluorescence quantum yields Journal of Chemical Society, Faraday Transactions 94 19 1998 2919 2922