The synthesis and optical properties of benzothiazole-based derivatives with various π-electron donors as novel bipolar fluorescent compounds

Dyes and Pigments

Volumn 86, Issue 3, 2010, Pages 238-248

  Wang, Haiying ^a   Chen, Gang ^a   Xu, Xiaoping ^a   Chen, Hua ^a   Ji, Shunjun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Bridge; Benzothiazole; Bipolar; Chemical calculation; Electrochemical; Optical

Indexed keywords

BENZOTHIAZOLES; BIPOLAR; CHEMICAL CALCULATIONS; ELECTRON DONORS; ELECTRON-ACCEPTING MOIETIES; ELECTRON-DONATING; FLUORESCENCE QUANTUM YIELD; FLUORESCENT COMPOUNDS; GROUND STATE GEOMETRY; HIGH THERMAL STABILITY; HIGHEST OCCUPIED MOLECULAR ORBITAL; LOWEST UNOCCUPIED MOLECULAR ORBITAL; OPTOELECTRONIC PROPERTIES; QUANTUM CHEMICAL CALCULATIONS; SPATIAL DISTRIBUTION;

CHEMICAL COMPOUNDS; ELECTROCHEMICAL PROPERTIES; ELECTRONS; FLUORESCENCE; MASS SPECTROMETRY; MOLECULAR MODELING; MOLECULAR ORBITALS; QUANTUM THEORY; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

OPTICAL PROPERTIES;

ELECTROCHEMISTRY; FLUORESCENCE; MOLECULAR STRUCTURE; OPTICAL PROPERTY; ORGANIC DYE; SYNTHESIS; THERMAL STABILITY;

EID: 77950861632     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2010.01.010     Document Type: Article

References (67)

1. Mullen K. Organic light emitting devices: synthesis properties and applications 2006, Wiley-VCH, Weinheim, Germany.
2. Tang C.W., Vanslyke S.A. Organic electroluminescent diodes. Applied Physics Letters 1987, 51(12):913-915.
3. Berresheim A.J., Muller M., Mullen K. Polyphenylene nanostructures. Chemical Reviews 1999, 99(7):1747-1785.
4. Shirota Y. Photo- and electroactive amorphous molecular materials-molecular design, syntheses, reactions, properties, and applications. Journal of Materials Chemistry 2005, 15:75-93.
5. Jenekhe S.A. Excited-state complexes of conjugated polymers. Advanced Materials 1995, 7(3):309-311.
6. Kraft A., Grimsdale A.C., Holmes A.B. Electroluminescent conjugated polymers-seeing polymers in a new light. Angewandte Chemie International Edition 1998, 37(4):402-428.
7. Hide F., Diaz-Garcia M.A., Schartz B.J., Heeger A.J. New developments in the photonic applications of conjugated polymers. Accounts of Chemical Research 1997, 30(10):430-436.
8. Gaylord B.S., Wang S., Heeger A.J., Bazan G.C. Water-soluble conjugated oligomers: effect of chain length and aggregation on photoluminescence-quenching efficiencies. Journal of the American Chemical Society 2001, 123(26):6417-6420.
9. Ng M.K., Lee D.C., Yu L. Molecular diodes based on conjugated diblock co-oligomers. Journal of the American Chemical Society 2002, 124(40):11862-11863.
10. Panda P., Veldman D., Sweelssen J., Bastiaansen J.J.A.M., Langeveld-Voss B.M.W., Meskers S.C.J. Charge transfer absorption for π-conjugated polymers and oligomers mixed with electron acceptors. Journal of Physical Chemistry B 2007, 111(19):5076-5081.
11. Mitschke U., Baüerle P. The electroluminescence of organic materials. Journal of Materials Chemistry 2000, 10(7):1471-1507.
12. Thompson B.C., Frechet J.M.J. Polymer-fullerene composite solar cells. Angewandte Chemie International Edition 2008, 47(1):58-77.
13. Di C.A., Yu G., Liu Y., Zhu D. High-performance organic field-effect transistors: molecular design, device fabrication, and physical properties. Journal of Physical Chemistry B 2007, 111(51):14083-14096.
14. Ning Z.J., Tian H. Triarylamine: a promising core unit for efficient photovoltaic materials. Chemical Communication 2009, 5483-5495.
15. Aziz H., Popovic Z.D., Hu N.X., Hor A.M., Xu G. Degradation mechanism of small molecule-based organic light-emitting devices. Science 1999, 283:1900-1902.
16. Andrew C.G., Khai L.C., Rainer E.M., Pawel G.J., Andrew B.H. Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Chemical Reviews 2009, 109(3). 897-1091.
17. Gregory H., Martin R.B. Electron-transporting materials for organic electroluminescent and electrophosphorescent devices. Journal of Materials Chemistry 2005, 15(1):94-107.
18. Yoon K.R., Ko S.O., Lee S.M., Lee H. Synthesis and characterization of carbazole derived nonlinear optical dyes. Dyes and Pigment 2007, 75:567-573.
19. Garnier F. Organic-based electronics à la carte. Accounts of Chemical Research 1999, 32(3):209-215.
20. Jones B.A., Ahrens M.J., Yoon M.H., Facchetti A., Marks T.J., Wasielewski M.R. High-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides). Angewandte Chemie International Edition 2004, 43(46):6363-6366.
21. Katz H.E., Bao Z.N., Gilat S.L. Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors. Accounts of Chemical Research 2001, 34(5):359-369.
22. Shirota Y., Kageyama H. Charge carrier transporting molecular materials and their applications in devices. Chemical Reviews 2007, 107(4):953-1010.
23. Roncali J. Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chemical Reviews 1992, 92(4):711-738.
24. Burgi L., Turbiez M., Pfeiffer R., Bienewald F., Kirner H.J., Winnewisser C. High-mobility ambipolar near-Infrared light-emitting polymer field-effect transistors. Advanced Materials 2008, 20(11):2217-2224.
25. Zhang Q., Ning Z., Tian H. 'Click' synthesis of starburst triphenylamine as potential emitting material. Dyes and Pigment 2009, 81:80-84.
26. Kamtekar K.T., Wang C., Bettington S., Batsanov A.S., Perepichka I.F., Bryce M.R., et al. New electroluminescent bipolar compounds for balanced charge-transport and tuneable colour in organic light emitting diodes: triphenylamine-oxadiazole-fluorene triad molecules. Journal of Materials Chemistry 2006, 16(32):3823-3835.
27. Hancock J.M., Gifford A.P., Zhu Y., Lou Y., Jenekhe S.A. n-Type conjugated oligoquinoline and oligoquinoxaline with triphenylamine endgroups: efficient ambipolar light emitters for device applications. Chemistry of Materials 2006, 18(20):4924-4932.
28. Xu X., Chen S., Yu G., Di C., You H., Ma D., et al. High-efficiency blue light-emitting diodes based on a polyphenylphenyl compound with strong electron-accepting groups. Advanced Materials 2007, 19(9):1281-1285.
29. Haung T.H., Lin J.T., Chen L.Y., Lin Y.T., Wu C.C. Dipolar dibenzothiophene S, S-dioxide derivatives containing diarylamine: materials for single-layer organic light-emitting devices. Advanced Materials 2006, 18(5):602-609.
30. Izumi T., Kobashi S., Takimiya K., Aso Y., Otsubo T. Synthesis and spectroscopic properties of a series of β-blocked long oligothiophenes up to the 96-mer: revaluation of effective conjugation length. Journal of the American Chemical Society 2003, 125(18):5286-5287.
31. Wang H.Y., Chen G., Liu Y., Hu L.H., Xu X.P., Ji S.J. The synthesis and characterization of novel dipolar fluorescent materials based on a quinoxaline core. Dyes and Pigments 2009, 83:269-275.
32. Meier H., Gerold J., Kolshorn H., Muhling B. Extension of conjugation leading to bathochromic or hypsochromic effects in OPV series. Chemistry-A European Journal 2004, 10(2):360-370.
33. Ning Z.J., Zhang Q., Pei H.C., Luan J.F., Lu C.G., Cui Y.P., et al. Photovoltage improvement for dye-sensitized solar cells via cone-shaped structural design. The Journal of Physical Chemistry 2009, 113:10307-10313.
34. Yamaguchi Y., Tanaka T., Kobayashi S., Wakamiya T., Matsubara Y., Yoshida Z. Light-emitting efficiency tuning of rod-shaped π conjugated systems by donor and acceptor groups. Journal of the American Chemical Society 2005, 127(26):9332-9333.
35. Wong M.S., Li Z.H., Tao Y., D'Iorio M. Synthesis and functional properties of donor-acceptor π-conjugated oligomers. Chemistry of Materials 2003, 15(5):1198-1203.
36. Candeias L.P., Gelinck G.H., Piet J.J., Piris J., Wegewijs B., Peeters E., et al. Substituent effects on the excited states of phenyl-capped phenylene vinylene tetramers. Synthetic Metals 2001, 119(2):339-340.
37. Strehmel B., Sarker A.M., Malpert J.H., Strehmel V., Seifert H., Neckers D.C. Effect of aromatic ring substitution on the optical properties, emission dynamics, and solid-state behavior of fluorinated oligophenylenevinylenes. Journal of the American Chemical Society 1999, 121(6):1226-1236.
38. Schweikart K.H., Hanack M., Luer L., Oelkrug D. Synthesis, absorption and luminescence of a new series of soluble distyrylbenzenes featuring cyano substituents at the peripheral rings. European Journal of Organic Chemistry 2001, 2:293-302.
39. Tanaka S., Yamashita Y. A novel monomer candidate for intrinsically conductive organic polymers based on nonclassical thiophene. Synthetic Metals 1997, 84(2):229-232.
40. Sonar P., Singh S.P., Leclère P., Surin M., Lazzaroni R., Lin T.T., et al. Synthesis, characterization and comparative study of thiophene-benzothiadiazole based donor-acceptor-donor (D-A-D) materials. Journal of Materials Chemistry 2009, 19(20):3228-3237.
41. Habrard F., Ouisse T., Stephan O., Aubouy L., Gerbier P., Hirsch L., et al. Organic light-emitting diodes and organic light-emitting electrochemical cells based on silole-fluorene derivatives. Synthetic Metals 2006, 156(19):1262-1270.
42. Lee T.H., Tong K.L., So S.K., Leung L.M. Synthesis and electroluminescence of thiophene-based bipolar small molecules with different arylamine moieties. Synthetic Metals 2005, 155(1):116-124.
43. Kannan R. Diphenylaminofluorene-based two-photon-absorbing chromophores with various π-electron acceptors. Chemistry of Materials 2001, 13(5):1896-1904.
44. Dichtel W.R., Serin J.M., Edder C., Fréchet J.M.J., Matuszewski M., Tan L.S., et al. Singlet oxygen generation via two-photon excited FRET. Journal of the American Chemical Society 2004, 126(17):5380-5381.
45. Cao D.X., Fang Q., Wang D., Liu Z.Q., Xue G., Xu G.B., et al. Synthesis and two-photon-excited fluorescence of benzothiazole-based compounds with various π-electron donors. European Journal of Organic Chemistry 2003, 18:3628-3636.
46. Thomas K.R.J., Lin J.T., Tao Y.T., Ko C.K. Light-emitting carbazole derivatives: potential electroluminescent materials. Journal of the American Chemical Society 2001, 123(38):9404-9411.
47. Brunner K., Dijken A.V., Börner H., Bastiaansen J.J.A.M., Kiggen N.M.M., Langeveld B.M.W. Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes: tuning the HOMO level without influencing the triplet energy in small molecules. Journal of the American Chemical Society 2004, 126(19):6035-6042.
48. Zhang Y., Wada T., Wang L., Sasabe H. Amorphous conjugated carbazole trimers for photorefractive materials. Chemistry of Materials 1997, 9(12):2798-2804.
49. Zhang Q., Chen J., Wang L. Novel hole-transporting materials based on 1,4-bis(carbazolyl)benzene for organic light-emitting devices. Journal of Materials Chemistry 2004, 14(5):895-900.
50. Kawashita Y., Ueba C., Masahiko M. A simple synthesis of 2-arylbenzothiazoles and its application to palladium-catalyzed Mizoroki-Heck reaction. Tetrahedron Letter 2006, 47(25):4231-4233.
51. Brembilla A., Roizard D., Lochon P. 1-methyl-2-pyrrolidinone: a well-adapted solvent in the benzothiazoles synthesis. Synthetic Communications 1990, 20(21):3379-3384.
52. Ha C., Horner J.H., Newcomb M., Varlick T.R., Arnold B.R., Lusztyk J. Kinetic studies of the cyclization of the 6,6-diphenyl-5-hexenyl radical. A test of the accuracy of rate constants for reactions of hydrogen transfer agents. Journal of Organic Chemistry 1993, 58(5):1194-1198.
53. Lee H.J., Sohn J., Hwang J., Young S., Choi P.H., Cha M. Triphenylamine-cored bifunctional organic molecules for two-photon absorption and photorefraction. Chemistry of Materials 2004, 16(3):456-465.
54. Miyaura N., Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chemical Reviews 1995, 95(7):2457-2483.
55. Ge Z., Hayakawa T., Ando S., Ueda M., Akiike T., Miyamoto H., et al. Solution-processible bipolar triphenylamine-benzimidazole derivatives for highly efficient single-layer organic light-emitting diodes. Chemistry of Materials 2008, 20(7):2532-2537.
56. Qian Y., Meng K., Lu C.G., Lin B.P., Huang W., Cui Y.P. The synthesis, photophysical properties and two-photon absorption of triphenylamine multipolar chromophores. Dyes and Pigments 2009, 80(1):174-180.
57. Takizawa S., Montes V.A., Anzenbacher P. Phenylbenzimidazole-based new bipolar host materials for efficient phosphorescent organic light-emitting diodes. Chemistry of Materials 2009, 21(12):2452-2458.
58. Li Y., Ding J., Day M., Tao Y., Lu J., Diorio M. Synthesis and properties of random and alternating fluorene/carbazole copolymers for use in blue light-emitting devices. Chemistry of Materials 2004, 16(11):2165-2173.
59. Zhao Z., Xu X., Jiang Z., Lu P., Yu G., Liu Y. Oligo(2,7-fluorene ethynylene)s with pyrene moieties: synthesis, characterization, photoluminescene, and electroluminescene. Journal of Organic Chemistry 2007, 72(22):8345-8353.
60. Janietz S., Bradley D.D.C., Grell M., Giebeler C., Inbaselatan M., Woo E.P. Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene). Applied Physics Letters 1998, 73(17):2453-2455.
61. Pommerehne J., Vestweber H., Guss W., Mahrt R.F., Bässler H., Porsch M., et al. Efficient two layer LEDs on a polymer blend basis. Advanced Materials 1995, 7(6):551-554.
62. Tao S., Li L., Yu J., Jiang Y., Zhou Y., Lee C.S., et al. Bipolar molecule as an excellent hole-transporter for organic-light emitting devices. Chemistry of Materials 2009, 21(7):1284-1287.
63. Ning Z., Zhang Q., Wu W., Pei H., Liu B., Tian H. Starburst triarylamine based dyes for efficient dye-sensitized solar cells. Journal of Organic Chemistry 2008, 73(10):3791-3797.
64. Frisch M.J., Trucks G.W., Schlegel H.B., Gill P.M.W., Johnson B.G., Robb M.A. Gaussian 03, revision C.01 2004, Gaussian, Inc., Pittsburgh, PA.
65. Acar N., Kurzawa J., Fritz N., Stockmann A., Roman C., Schneider S., et al. Phenothiazine-pyrene dyads: photoinduced charge separation and structural relaxation in the CT state. Journal of Physical Chemistry A 2003, 107(45):9530-9541.
66. Elangovan A., Kao K.M., Yang S.W., Chen Y.L., Ho T.I., Su Y.L.O. Synthesis, electronic properties, and electrochemiluminescence of donor-substituted phenylethynylanthronitriles. Journal of Organic Chemistry 2005, 70(11):4460-4469.
67. Marsden J.A., Miller J.J., Shirtcliff L.D., Haley M.M. Structure-property relationships of donor/acceptor-functionalized tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes. Journal of the American Chemical Society 2005, 127(8):2464-2476.