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Synthesis of two carbazole-based dyes and application of two-photon initiating polymerization

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Abstract

Two carbazole-based polymerization initiators possessing blue fluorescence emission have been synthesized via Wittig reaction in the solid phase at room temperature. Two-photon excited fluorescence (TPEF) spectra for them were investigated under 800 nm fs laser pulse and two-photon absorption cross sections were determined by the Z-scan technique. Then two-photon initiating polymerization (TPIP) microfabrication experiments were successfully carried out. Three-dimensional lattice and artificial defects were gained, indicating that they were viable candidates for the two-photon polymerization initiator in practical application of microfabrication.

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References

  1. Abbotto A, Beverina L, Bozio R, Bradamante S, Ferrante C, Pagani G A, Signorini R. Push-pull organic chromophores for the frequency-upconverted lasing. Adv Mater, 2000, 12: 1963–1967

    Article  CAS  Google Scholar 

  2. He G S, Markowicz P P, Lin T C, Prasad P N. Observation of stimulated emission by direct three-photon excitation. Nature, 2002, 415: 767–770

    CAS  Google Scholar 

  3. Wang Y, He G S, Prasad P N, Goodson T III. Ultrafast dynamics in multibranched structures with enhanced two-photon absorption. J Am Chem Soc, 2005, 127: 10128–10129

    Article  CAS  Google Scholar 

  4. Goodson T III. Optical excitations in organic dendrimers investigated by time-resolved and nonlinear spectroscope. Acc Chem Res, 2005, 38: 99–107

    Article  CAS  Google Scholar 

  5. Yuste R, Denk W. Dendritic spines as basic functional units of neuronal integration. Nature, 1995, 375: 682–684

    Article  CAS  Google Scholar 

  6. Kurtz R, Fricke M, Kalb J, Tinnefeld P, Sauer M J. Applications of multiline of two-photon microscope to functional in vivo imaging. Neurosci Meth, 2006, 151: 276–286

    Article  Google Scholar 

  7. Zhou W, Kuebler S M, Braun K L, Yu T, Cammack J K, Ober C K, Perry J W, Marder S R. An efficient two-photon-generated photoacid applied to positive-tone 3D microfabrication. Science, 2002, 296: 1106–1109

    Article  CAS  Google Scholar 

  8. Cumpston B H, Ananthavel S P, Barlow S, Dyer D L, Ehrlich J E, Erskine L L, Heikal A A, Kuebler S M, Lee I Y S, McCord-Maughon D, Qin J Q, Röckel H, Rumi M, Wu X L, Marder S R, Perry J W. Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication. Nature, 1999, 398: 51–54

    Article  CAS  Google Scholar 

  9. He G S, Tan L S, Zheng Q D, Prasad P N. Multiphoton absorption materials: Molecular designs, characterizations, and applications. Chem Rev, 2008, 108: 1245–1330

    Article  CAS  Google Scholar 

  10. Lee S, Justin-Thomas K R, Thayumanavan S, Christopher J B. Dependence of the two-photon absorption cross section on the conjugation of the phenylacetylene linker in dipolar donor-bridge-acceptor chromophores. J Phys Chem A, 2005, 109: 9767–9774

    Article  CAS  Google Scholar 

  11. Yan Y X, Tao X T, Xu G B, Yang J X, Ren Y, Zhao X, Wu Y Z, Yu X Q, Jiang M H. Synthesis and nonlinear optical properties of novel multi-branched two-photon polymerization initiators. J Mater Chem, 2004, 14: 2995–3000

    Article  CAS  Google Scholar 

  12. Zhou H P, Li D M, Zhang J Z, Zhu Y M, Wu J Y, Hu Z J, Xu G B, Tian Y P, Xie Y, Tao X T, Jiang M H, Tao L M, Guo Y H, Wang C K. Crystal structures, optical properties and theoretical calculation of novel two-photon polymerization initiators. Chem Phys, 2006, 322: 459–470

    Article  CAS  Google Scholar 

  13. Yoon K R, Ko S O, Lee S M, Lee H. Synthesis and characterization of carbazole derived nonlinear optical dyes. Dyes Pigm, 2007, 75: 567–573

    Article  CAS  Google Scholar 

  14. Qian Y. 3,6-Disubstituted carbazole chromophores containing thiazole and benzothiazole units: Synthesis, characterization and firstorder hyperpolarizabilities. Dyes Pigm, 2008, 76: 277–281

    Article  CAS  Google Scholar 

  15. Liu C G, Qiu Y Q, Su Z M, Yang G C, Sun S L. Computational study on second-order nonlinear response of a series of two-dimensional carbazole-cored chromophores. J Phys Chem C, 2008, 112: 7021–7028

    Article  CAS  Google Scholar 

  16. Maruyama S, Tao X T, Hokari H, Noh T, Zhang Y D, Wada T, Sasabe H, Suzuki H, Watanabe T, Miyata S. Electroluminescent applications of a cyclic carbazole oligomer. J Mater Chem, 1999, 9: 893–898

    Article  CAS  Google Scholar 

  17. Bredereck H, Simchen G, Griebenow W. Synthese und reaktionen von[α-(dimethylaminomethylen)-benzyl]triphenylphosphonium-salzen. Chem Ber, 1973, 106: 3732–3742

    Article  CAS  Google Scholar 

  18. Demas J N, Crosby G A. Measurement of photoluminescence quantum yields. J Phys Chem, 1971, 75: 991–1024

    Article  Google Scholar 

  19. Woo H Y, Liu B, Kohler B, Korystov D, Mikhailovsky A, Guillermo C B. Solvent effects on the two-photon absorption of distyrylbenzene chromophores. J Am Chem Soc, 2005, 127: 14721–14729

    Article  CAS  Google Scholar 

  20. Wu L Z, Tang X J, Jiang M H, Tang C H. Two-photon induced fluorescence of novel dyes. Chem Phys Lett, 1999, 315: 379–382

    Article  CAS  Google Scholar 

  21. Zhao W, Paltty-Muhoray P. Z-scan measurement of χ(3) using top-hat beams. Appl Phys Lett, 1994, 65: 673–675

    Article  CAS  Google Scholar 

  22. Zhou G Y, Wang X M, Wang D, Wang C, Shao Z S, Fang Q, Jiang M H. Two-photon absorption and nonlinear optical properties of a new organic dye PSPI. Opt Commun, 2001, 190: 345–349

    Article  CAS  Google Scholar 

  23. Sun H B, Kawakami T, Xu Y, Ye J Y, Matuso S, Misawa H, Miwa M, Kaneko R. Real three-dimensional microstructures fabricated by photopolymerization of resins through two-photon absorption. Opt Lett, 2000, 25: 1110–1112

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui University, Hefei, 230039, China

    RenTao Hu, LiangFei Lü, BanFeng Ruan, Peng Wang, MingLiang Zhang, HongPing Zhou, ShengLi Li, JieYing Wu & YuPeng Tian

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  1. RenTao Hu
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  2. LiangFei Lü
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  3. BanFeng Ruan
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  4. Peng Wang
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  5. MingLiang Zhang
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  6. HongPing Zhou
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  7. ShengLi Li
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  8. JieYing Wu
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Corresponding authors

Correspondence to JieYing Wu or YuPeng Tian.

Additional information

Supported by the National Natural Science Foundation of China (Grant Nos. 50532030, 20771001 & 50703001), and Team for Scientific Innovation of Anhui Province (Grant No. 2006KJ007TD)

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Hu, R., Lü, L., Ruan, B. et al. Synthesis of two carbazole-based dyes and application of two-photon initiating polymerization. Sci. China Ser. B-Chem. 52, 1210–1215 (2009). https://doi.org/10.1007/s11426-009-0039-6

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  • DOI: https://doi.org/10.1007/s11426-009-0039-6

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