Absorption and fluorescence spectroscopic properties of 1- and 1,4-silyl-substituted naphthalene derivatives

Molecules

Volumn 17, Issue 5, 2012, Pages 5108-5125

  Maeda, Hajime ^a   Maeda, Tomohiro ^b   Mizuno, Kazuhiko ^b  

^a KANAZAWA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Absorption; Fluorescence; Fluorescence lifetime; Fluorescence quantum yield; Fluorescence quenching; Naphthalene; Organosilicon compounds

Indexed keywords

9,10 DICYANOANTHRACENE; 9,10-DICYANOANTHRACENE; ANTHRACENE DERIVATIVE; FLUORESCENT DYE; HYDROGEN; NAPHTHALENE DERIVATIVE; NITRILE; ORGANOSILICON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; SPECTROFLUOROMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ANTHRACENES; FLUORESCENCE; FLUORESCENT DYES; HYDROGEN; MOLECULAR STRUCTURE; NAPHTHALENES; NITRILES; ORGANOSILICON COMPOUNDS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84861490266     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17055108     Document Type: Article

References (53)

1. Steinmetz, M.G. Organosilane Photochemistry. Chem. Rev. 1995, 95, 1527-1588.
2. Miller, R.D.; Michl, J. Polysilane High Polymers. Chem. Rev. 1989, 89, 1359-1410.
3. West, R.; Fink, M.J.; Michl, J. Tetramesityldisilene, a Stable Compound Containing a Silicon- Silicon Double Bond. Science 1981, 214, 1343-1344.
4. Murakami, S.; Collins, S.; Masamune, S. Photo-Induced Fragmentation of Tri-t-butyltrimethylsilylcyclotrisilanes and E,Z-Interconversion of Di-t-butyldimethylsilyldisilenes. Tetrahedron Lett. 1984, 25, 2131-2134.
5. Michalczyk, M.J.; West, R.; Michl, J. Kinetics of Thermal Cis-Trans Isomerizations in Disilenes. Organometallics 1985, 4, 826-829.
6. Dewan, J.C.; Murakami, S.; Snow, J.T.; Collins, S.; Masamune, S. Crystal Structures of Two Isomeric Cyclotrisilanes. J. Chem. Soc. Chem. Commun. 1985, 892-894.
7. Yokelson, H.B.; Maxka, J.; Siegel, D.A.; West, R. 29Si NMR Observation of an Unprecedented Rearrangement in Tetraaryldisilenes. J. Am. Chem. Soc. 1986, 108, 4239-4241.
8. Shepherd, B.D.; Powell, D.R.; West, R. Synthesis, Geometrical Isomerism, and Crystal Structure of a Highly Hindered Disilene. Organometallics 1989, 8, 2664-2669.
9. Shizuka, H.; Sato, Y.; Ueki, Y.; Ishikawa, M.; Kumada, M. The 2pp*-3dp Interaction in Aromatic Silanes. J. Chem. Soc. Faraday Trans. 1 1984, 80, 341-357.
10. Sakurai, H. Structure and reaction controlled by strong sigma/pi interactions. Pure Appl. Chem. 1987, 59, 1637-1646.
11. Yoon, U.C.; Mariano, P.S. Mechanistic and Synthetic Aspects of Amine-Enone Single Electron Transfer Photochemistry. Acc. Chem. Res. 1992, 25, 233-240.
12. Mizuno, K.; Tamai, T.; Sugimoto, A.; Maeda, H. Photoinduced Electron Transfer Reactions of Organosilicon Compounds. In Advances in Electron Transfer Chemistry, Mariano, P.S., Ed.; JAI Press: London, UK, 1999; Volume 6, pp. 131-165.
13. Tamai, T.; Hayamizu, T.; Mizuno, K. Photoinduced Electron Transfer Reactions of Organosilicon Compounds. In Handbook of Photochemistry and Photobiology; Nalwa, H.S., Ed.; American Scientific Publishers: Stevenson Ranch, CA, USA, 2003; pp. 125-156.
14. Mizuno, K.; Hayamizu, T.; Maeda, H. Regio- and stereoselective functionalization of electron-deficient alkenes by use of organosilicon compounds via photoinduced electron transfer. Pure Appl. Chem. 2003, 75, 1049-1054.
15. Daney, M.; Vanucci, C.; Desvergne, J.-P.; Castellan, A.; Bouas-Laurent, H. Photochemistry of Bichromophoric Systems. Silicon Guided Intramolecular 9,10:1',2' Anthracene Photodimerization in Bis(9-anthryl)dimethylsilane. Tetrahedron Lett. 1985, 26, 1505-1508.
16. Desvergne, J.-P.; Bitit, N.; Castellan, A.; Webb, M.; Bouas-Laurent, H. Non-conjugated Bichromophoric Systems. Part 4. Synthesis and Photochemical Study of Bis-9-anthryls with a Four-membered Chain; Influence of the Replacement of Methylene Links by Oxygen Atoms or Dimethylsilyl Groups on the Formation of Intramolecular Excimers and Photocyclomers. J. Chem. Soc. Perkin Trans. 2 1988, 1885-1894.
17. Declercq, D.; De Schryver, F.C.; Miller, R.D. Fluorescence behaviour of pyrene substituted triand hexa-silanes. Chem. Phys. Lett. 1991, 186, 467-473.
18. Molecules 2012, 17 5123
19. Declercq, D.; Delbeke, P.; De Schryver, F.C.; Van Meervelt, L.; Miller, R.D. Ground- and Excited-State Interactions in Di-1-pyrenyl-Substituted Oligosilanes. J. Am. Chem. Soc. 1993, 115, 5702-5708.
20. Suzuki, H.; Satoh, S.; Kimata, Y.; Kuriyama, A. Synthesis and Properties of Poly(methylphenylsilane) Containing Anthracene Units. Chem. Lett. 1995, 451-452.
21. Kyushin, S.; Ikarugi, M.; Goto, M.; Hiratsuka, H.; Matsumoto, H. Synthesis and Electronic Properties of 9,10-Didilylanthracenes. Organometallics 1996, 15, 1067-1070.
22. Yamaguchi, S.; Akiyama, S.; Tamao, K. Synthesis, Structures, Photophysical Properties, and Dynamic Stereochemistry of Tri-9-anthrylsilane Derivatives. Organometallics 1998, 17, 4347-4352.
23. Desvergne, J.-P.; Bonneau, R.; Dörr, G.; Bouas-Laurent, H. Photoprotodesilylation of 9-trimethylsilylanthracene in alcohols. Photochem. Photobiol. Sci. 2003, 2, 289-296.
24. Kyushin, S.; Takemasa, N.; Matsumoto, H.; Horiuchi, H.; Hiratsuka, H. 2,3,6,7,10,11- Hexakis(dimethylsilyl)triphenylene. Chem. Lett. 2003, 32, 1048-1049.
25. Karatsu, T.; Hazuku, R.; Nishioka, D.; Yagai, S.; Kobayashi, N.; Kitamura, A. Photoluminescence and Electroluminescence of 9,10-Bis(silylethynyl) anthracene. J. Photopolym. Sci. Tech. 2005, 18, 65-68.
26. Kyushin, S.; Ishikita, Y.; Matsumoto, H.; Horiuchi, H.; Hiratsuka, H. Yellow-green Fluorescence of 5,11- and 5,12-Bis(diisopropylsilyl)naphthacenes. Chem. Lett. 2006, 35, 64-65.
27. Kyushin, S.; Matsuura, T.; Matsumoto, H. 2,3,4,5-Tetrakis(dimethylsilyl) thiophene: The First 2,3,4,5-Tetrasilylthiophene. Organometallics 2006, 25, 2761-2765.
28. Bénard, C.P.; Geng, Z.; Heuft, M.A.; VanCrey, K.; Fallis, A.G. Double Diels-Alder Strategies to Soluble 2,9- and 2,9,6,13- Tetraethynylpentacenes, Photolytic [4 + 4] Cycloadditions, and Pentacene Crystal Packing. J. Org. Chem. 2007, 72, 7229-7236.
29. Karatsu, T.; Hazuku, R.; Asuke, M.; Nishigaki, A.; Yagai, S.; Suzuri, Y.; Kita, H.; Kitamura, A. Blue electroluminescence of silyl substituted anthracene derivatives. Org. Electronics 2007, 8, 357-366.
30. Asai, K.; Konishi, G.; Nakajima, Y.; Kawauchi, S.; Ozawa, F.; Mizuno, K. Enhanced absorption and fluorescence efficiency of silylethynyl-functionalized oligothiophenes and thieno[3,2-b]thiophene. J. Organomet. Chem. 2011, 696, 1266-1271.
31. Maeda, H.; Inoue, Y.; Ishida, H.; Mizuno, K. UV Absorption and Fluorescence Properties of Pyrene Derivatives Having Trimethylsilyl, Trimethylgermyl, and Trimethylstannyl Groups. Chem. Lett. 2001, 1224-1225.
32. Maeda, H.; Maeda, T.; Mizuno, K.; Fujimoto, K.; Shimizu, H.; Inouye, M. Alkynylpyrenes as Improved Pyrene-Based Biomolecular Probes with the Advantages of High Fluorescence Quantum Yields and Long Absorption/Emission Wavelengths. Chem. Eur. J. 2006, 12, 824-831.
33. Ara, A.M.; Iimori, T.; Nakabayashi, T.; Maeda, H.; Mizuno, K.; Ohta, N. Electric Field Effects on Absorption and Fluorescence Spectra of Trimethylsilyl- and Trimethylsilylethynyl-Substituted Compounds of Pyrene in a PMMA Film. J. Phys. Chem. B 2007, 111, 10687-10696.
34. Tamai, T.; Watanabe, M.; Maeda, H.; Mizuno, K. Fluorescence Polymer Particles Incorporating Pyrene Derivatives. J. Polym. Sci. Part A Polym. Chem. 2008, 46, 1470-1475.
35. Maeda, H.; Ishida, H.; Inoue, Y.; Merpuge, A.; Maeda, T.; Mizuno, K. UV absorption and fluorescence properties of fused aromatic hydrocarbons having trimethylsilyl, trimethylgermyl, and trimethylstannyl groups. Res. Chem. Intermed. 2009, 35, 939-948.
36. Pitt, C.G.; Carey, R.N.; Toren, E.C., Jr. Nature of the Electronic Interactions in Aryl-Substituted Polysilanes. J. Am. Chem. Soc. 1972, 94, 3806-3811.
37. Ishikawa, M.; Oda, M.; Miyoshi, N.; Fábry, L.; Kumada, M.; Yamabe, T.; Akagi, K.; Fukui, K. Photochemically Generated Silicon-Carbon Double-Bonded Intermediates. 10. Photochemical Behavior of 1-Disilanyl- and 2-Disilanylnaphthalenes. J. Am. Chem. Soc. 1979, 101, 4612-4618.
38. Shizuka, H.; Obuchi, H.; Ishikawa, M.; Kumada, M. Photochemical and Photophysical Behaviour of Phenylsilanes and Naphthylsilanes. J. Chem. Soc. Faraday Trans. 1 1984, 80, 383-401.
39. Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Minato, A. Silicon-Carbon Unsaturated Compounds. 26. Photochemical Behavior of 1,4- and 1,5-Bis(pentamethyldisilanyl)naphthalene. Organometallics 1991, 10, 880-887.
40. Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Tsukihara, T.; Takahashi, K.; Kiso, Y. Silicon-Carbon Unsaturated Compounds. 29. Photochemical Behavior of 2,6- and 2,7-Bis(pentamethyldisilanyl) naphthalene. Organometallics 1991, 10, 2685-2695.
41. Karatsu, T.; Shibata, T.; Nishigaki, A.; Fukui, K.; Kitamura, A. p-p and s-p Interactions in a,w-Dinaphthyl and -Dianthryl Oligosilanes in Solution. Chem. Lett. 2001, 994-995.
42. Karatsu, T.; Shibata, T.; Nishigaki, A.; Kitamura, A.; Hatanaka, Y.; Nishimura, Y.; Sato, S.; Yamazaki, I. p-p and s-p Interactions in a,w-Di-(9-anthryl) and Di-(1-naphthyl) Oligosilanes Studied by Time-Resolved Fluorescence in Solution. J. Phys. Chem. B 2003, 107, 12184-12191.
43. Karatsu, T.; Terasawa, M.; Yagai, S.; Kitamura, A.; Nakamura, T.; Nishimura, Y.; Yamazaki, I. Time-resolved fluorescence of a-(9-anthryl)-w-(1- naphthyl)-oligosilanes: Intramolecular electronic energy and charge transfer through p-p and s-p interactions. J. Organomet. Chem. 2004, 689, 1029-1035.
44. Gerson, F.; Heinzer, J.; Bock, H.; Alt, H.; Seidl, H. ESR.-Messungen an Radikal-Anionen Trimethylsilyl-substituierter p-Elektronensysteme. Helv. Chim. Acta 1968, 51, 707-718.
45. Allred, A.L.; Bush, L.W. Electron Spin Resonance Studies of Silicon- and Germanium-Substituted Anion Radicals. J. Am. Chem. Soc. 1968, 90, 3352-3360.
46. Evans, A.G.; Jerome, B.; Rees, N.H. The dp-pp interaction in trimethylsilyl substituted naphthalenes. I. Study using polarography, andcharge transfer and ultraviolet spectroscopy. J. Chem. Soc. Perkin Trans. 2 1973, 447-452.
47. Evans, A.G.; Jerome, B.; Rees, N.H. dp-pp Interaction in Trimethylsilyl-substituted Naphthalenes. Part II. Electron Spin Resonance Studies. J. Chem. Soc. Perkin Trans. 2 1973, 2091-2093.
48. Sipe, H.J., Jr.; West, R. Electron Spin Resonance Studies of Group IV Organometallic Radical Anions. J. Organomet. Chem. 1974, 70, 353-366.
49. Kaim, W.; Tesmann, H.; Bock, H. Me3C-, Me3Si-, Me3Ge-, Me3Sn- und Me3Pb-substituierte Benzol- und Naphthalin-Derivate und ihre Radikalanionen. Chem. Ber. 1980, 113, 3221-3234.
50. Berlman, I.B. Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed.; Academic Press, Inc.: New York, NY, USA, 1971.
51. Eriksen, J.; Foote, C.S. Electron-Transfer Fluorescence Quenching and Exciplexes of Cyano- Substituted Anthracenes. J. Phys. Chem. 1978, 82, 2659-2662.
52. Mizuno, K.; Pac, C.; Sakurai, H. Photochemical Cyanation of Aromatic Hydrocarbons with Cyanide Anion. J. Chem. Soc. Chem. Commun. 1975, 553-553.
53. Yasuda, M.; Pac, C.; Sakurai, H. Photochemical Reactions of Aromatic Compounds. Part 34. Direct Photocyanation of Arenes with Sodium Cyanide in the Presence of Electron Acceptors. J. Chem. Soc. Perkin Trans. 1 1981, 746-750.