The facile synthesis of novel phenothiazine derivatives for blue, yellow-green, and red light emission

Dyes and Pigments

Volumn 83, Issue 2, 2009, Pages 180-186

  Li, Dongmei ^a   Lv, Liangfei ^a   Sun, Pingping ^a   Zhou, Wen ^a   Wang, Peng ^a   Wu, Jieying ^a   Kan, Yuhe ^b   Zhou, Hongping ^a   Tian, Yupeng ^a,c,d  

^a ANHUI UNIVERSITY   (China)

^b HUAIYIN NORMAL UNIVERSITY   (China)

^c SHANDONG UNIVERSITY   (China)

^d NANJING UNIVERSITY   (China)

Author keywords

Bis diketonate; Bis dioxaborines (DOBs); Heterocycles; Intramolecular charge transfer; Phenothiazine; Two photon absorption (TPA)

Indexed keywords

BIS-DIOXABORINES (DOBS); HETEROCYCLES; INTRAMOLECULAR CHARGE TRANSFER; PHENOTHIAZINE; TWO-PHOTON ABSORPTION (TPA);

ABSORPTION; CHARGE TRANSFER; ELECTROCHEMICAL PROPERTIES; EMISSION SPECTROSCOPY; FLUORESCENCE; INSECTICIDES; ION EXCHANGE; LIGHT ABSORPTION; LUMINESCENCE OF ORGANIC SOLIDS; MASS TRANSFER; OPTICAL MATERIALS; PHOTONS; SULFUR COMPOUNDS;

MULTIPHOTON PROCESSES;

ABSORPTION; FLUORESCENCE; ION EXCHANGE; PHYSICAL PROPERTY; SYNTHESIS;

EID: 67649385566     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.04.006     Document Type: Article

References (28)

1. Tian Y.P., Li L., Zhang J.Z., Yang J.X., Zhou H.P., Wu J.Y., et al. Investigations and facile synthesis of a series of novel multi-functional two-photon absorption materials. Journal of Materials Chemistry 17 (2007) 3646-3654
2. He G.S., Swiatkiewicz J., Jiang Y., Prasad P.N., Reinhardt B.A., Tan L.S., et al. Two-photon excitation and optical spatial-profile reshaping via a nonlinear absorbing medium. Journal of Physical Chemistry A 104 (2000) 4805-4810
3. Tian Y.P., Li L., Zhou Y.H., Wang P., Zhou H.P., Wu J.Y., et al. Design and synthesis of two new two-photon absorbing pyridine salts as ligands and their rare earth complexes. Crystal Growth & Design 9 (2009) 1499-1504
4. Gao Y.H., Wu J.Y., Li Y.M., Sun P.P., Zhou H.P., Yang J.X., et al. A sulfur-terminal Zn(II) complex and its two-photon microscopy biological imaging application. Journal of the American Chemical Society 131 (2009) 5208-5213
5. Roy I., Ohulchanskyy T.Y., Pudavar H.E., Bergey E.J., Oseroff A.R., Morgan J., et al. Ceramic-based nanoparticles entrapping water-insoluble photosensitizing anticancer drugs: a novel drug-carrier system for photodynamic therapy. Journal of the American Chemical Society 125 (2003) 7860-7865
6. He G.S., Tan L.S., Zheng Q., and Prasad P.N. Multiphoton absorbing materials: molecular designs, characterizations, and applications. Chemical Reviews 108 (2008) 1245-1330
7. Sainsbury M. In: Sainsbury M. (Ed). Rodd's chemistry of carbon compounds. 2nd ed. vol. 4 (1998), Elsevier, Amsterdam 575-608
8. Sainsbury M. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive heterocyclic chemistry vol. 3 (1984), Pergamon Press, Oxford 995
9. Kramer C.S., Zeitler K., and Muller T.J.J. Synthesis of functionalized ethynylphenothiazine fluorophores. Organic Letters 2 (2000) 3723-3726
10. García C., Oyola R., Piñero L.E., Arce R., Silva J., and Sánchez V. Substitution and solvent effects on the photophysical properties of several series of 10-alkylated phenothiazine derivatives. Journal of Physical Chemistry A 109 (2005) 3360-3371
11. Hauck M., Schönhaber J., Zucchero A.J., Hardcastle K.I., Müller T.J.J., and Bunz U.H.F. Phenothiazine cruciforms: synthesis and metallochromic properties. The Journal of Organic Chemistry 72 (2007) 6714-6725
12. 4 to the orange solution yielded the red oil. After removal of water, the product was precipitated by addition of petroleum ether (500 mL). Red solid was collected by filtration. The product was purified by chromatography on a silica gel with ethyl acetate/petroleum ether mixture (1:2 v/v) as the eluent. Red microcrystals were obtained (yield 60%). The details of the synthesis and characterization of 3 and 5 shall be reported by us soon.
13. Haugland RP. The handbook - a guide to fluorescent probes and labeling technologies. 10th ed.; 2005 [chapter 1, section 1.4].
14. Gorman A., Killoran J., O'Shea C., Kenna T., Gallagher W.M., and O'Shea D.F. In vitro demonstration of the heavy-atom effect for photodynamic therapy. Journal of the American Chemical Society 126 (2004) 10619-10631
15. 2 complexes as highly efficient and photostable laser dyes. Journal of Physical Chemistry A 108 (2004) 3315-3323
16. Chow Y.L., Johansson C.I., Zhang Y.H., Gautron R., Yang L., Rassat A., et al. Spectroscopic and electrochemical properties of 1,3-diketonatoboron derivatives. Journal of Physical Organic Chemistry 9 (1996) 7-16
17. Halik M., Wenseleers W., Grasso C., Stellacci F., Zojer E., Barlow S., et al. Bis(dioxaborine) compounds with large two-photon cross sections, and their use in the photodeposition of silver. Chemical Communications (2003) 1490-1491
18. Domercq B., Grasso C., Maldonado J., Halik M., Barlow S., Marder S.R., et al. Electron-transport properties and use in organic light-emitting diodes of a bis(dioxaborine)fluorene derivative. Journal of Physical Chemistry B 108 (2004) 8647-8651
19. Xu C., and Webb W.W. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. Journal of the Optical Society of America B (Optical Physics) 13 (1996) 481-491
20. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 03, revision B.04 (2003), Gaussian, Inc., Pittsburgh, PA
21. 4] cluster: a density functional theory/time-dependent density functional theory investigation. Inorganic Chemistry 45 (2006) 10576-10584
22. Ovejero P., Mayoral M.J., Cano M., and Lagunas M.C. Luminescence of neutral and ionic gold(I) complexes containing pyrazole or pyrazolate-type ligands. Journal of Organometallic Chemistry 692 (2007) 1690-1697
23. Tian Y.P., Zhang M.L., Yu X.Q., Xu G.B., Ren Y., Yang J.X., et al. Two novel two-photon polymerization initiators with extensive application prospects. Chemical Physics Letters 388 (2004) 325-329
24. Woo H.Y., Liu B., Kohler B., Korystov D., Mikhailovsky A., and Bazan G.C. Solvent effects on the two-photon absorption of distyrylbenzene chromophores. Journal of the American Chemical Society 127 (2005) 14721-14729
25. Zhou H.P., Li D.M., Zhang J.Z., Zhu Y.M., Wu J.Y., Hu Z.J., et al. Crystal structures, optical properties and theoretical calculation of novel two-photon polymerization initiators. Chemical Physics 322 (2006) 459-470
26. Zhang X.J., Ren X.S., Xu Q.H., Loh K.P., and Chen Z.K. One- and two-photon turn-on fluorescent probe for cysteine and homocysteine with large emission shift. Organic Letters 11 (2009) 1257-1260
27. Ko C.W., Tao Y.T., Danel A., Krzemińska L., and Tomasik P. Organic light-emitting diodes based on 2-(stilben-4-yl)benzoxazole derivatives: an implication on the emission mechanism. Chemistry of Materials 13 (2001) 2441-2446
28. Swanson S.A., Wallraff G.M., Chen J.P., Zhang W., Bozano L.D., Carter K.R., et al. Stable and efficient fluorescent red and green dyes for external and internal conversion of blue OLED emission. Chemistry of Materials 15 (2003) 2305-2312