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A new series of two-photon polymerization initiators: Synthesis and nonlinear optical properties

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Abstract

Four photopolymerization initiators with D-π-D (D, donor; π, conjugation system) structure have been synthesized by solvent-free reaction and characterized by 1H NMR spectroscopy, IR and elemental analysis. The one-photon and two-photon excited fluorescence have been investigated in different solvents. Experimental results of the one-photon and two-photon absorption cross sections show different trends in OPA and TPA ability with different substitution groups in donor units.

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References

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

    Article  CAS  Google Scholar 

  2. Diaspro A, Robello M. Two photon excitation of fluorescence for three dimensional optical imaging of biological structures. J Photochem Photobiol B Biol, 2000, 55: 1–8

    Article  CAS  Google Scholar 

  3. Dyer D J, Cumpston B H, McCord-Maughon D, Thaynmanavan S, Barlow S, Perry J W, Marder S R. Turning on fluorescence by two-photon excitation and polymerization: Toward a 3-D optical memory device. Nonlinear Optics, Quantum Optics, 2004, 31: 175–184

    CAS  Google Scholar 

  4. Li X, Zhao Y X, Wang T, Shi M Q, Wu F P. Coumarin derivatives with enhanced two photon absorption cross-sections. Dyes Pigm, 2007, 74: 108–112

    Article  CAS  Google Scholar 

  5. Qian Y, Lu Z F, Lu C G, Chen Z M, Cui Y P. Synthesis and two-photon absorption properties of 2,5-bis[4-(2-arylvinyl)phenyl]-1,3,4-oxadiazoles. Dyes Pigm, 2007, 75: 641–646

    Article  CAS  Google Scholar 

  6. Wang Z M, Wang X M, Zhao J F, Jiang W L, Yang P, Fang X Y. Cooperative enhancement of two-photon absorption based on electron coupling in triphenylamine-branching chromophore. Dyes Pigm, 2008, 79: 145–152

    Article  CAS  Google Scholar 

  7. Terenziani F, le Droumaguet C, Katan C, Mongin O, Blanchard-Desce M. Effect of branching on two-photon absorption in triphenyl-benzene derivatives. ChemPhysChem, 2007, 8: 723–734

    Article  CAS  Google Scholar 

  8. Signorini R, Ferrante C, Pedron D, Zerbetto M, Cecchetto E, Slaviero M, Fortunati I, Collini E, Bozio R, Abbotto A, Beverina L, Pagani G A. Effective two-photon absorption cross section of heteroaromatic quadrupolar dyes: dependence on measurement technique and laser pulse characteristics. J Phys Chem A, 2008, 112: 4224–4234

    Article  CAS  Google Scholar 

  9. Tian Y Q, Chen C Y, Cheng Y J, Young A C, Tucker N M, Jen A K Y. Hydrophobic chromophores in aqueous micellar solution showing large two-photon absorption cross sections. Adv Funct Mater, 2007, 17: 1691–1697

    Article  CAS  Google Scholar 

  10. Fan H H, Chen X, Wang H Z, Tian Y P. Structure-property relationships in a new series of two-photon absorbing D-π-D divinyl-biphenyl derivatives. Chem Phys Lett, 2007, 436: 171–174

    Article  CAS  Google Scholar 

  11. Feng Y L, Yan Y L, Wang S, Zhu W H, Qian S X, Tian H. Photochromic thiophene oligomers based on bisthienylethene: syntheses, photochromic and two-photon properties. J Mater Chem, 2006, 16: 3685–3692

    Article  CAS  Google Scholar 

  12. Kato S I, Matsumoto T, Shigeiwa M, Gorohmaru H, Maeda S, Ishii I T, Mataka S. Novel 2,1,3-benzothiadiazole-based red-fluorescent dyes with enhanced two-photon absorption cross-sections. Chem Eur J, 2006, 12: 2303–2317

    Article  CAS  Google Scholar 

  13. Wang C K, Macak P, Luo Y. Effects of π centers and symmetry on two photon absorption cross sections of organic chromophores. J Chem Phys, 2001, 114: 9813–9820

    Article  CAS  Google Scholar 

  14. Bauer C, Schnabel B, Kley E B, Scherf U, Giessen H, Mahrt R F. Two-photon pumped lasing from a two-dimensional photonic band-gap structure with polymeric gain material. Adv Mater, 2002, 14: 673–676

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Ehrlich J, Wu X, Lee I Y S, Hu Z Y, Röckel H, Marder S R, Perry J. Two-photon absorbing for biological imaging. Opt Lett, 1997, 22: 1843–1845

    Article  CAS  Google Scholar 

  17. Kawatta S, Kawatta Y. Three-dimensional optical data storage using photochromic materials. Chem Rev, 2000, 100: 1777–1788

    Article  Google Scholar 

  18. Ogawa K, Hasegawa H, Inaba Y, Kobuke Y, Inouye H, Kanemitsu Y, Kohno E, Hirano T, Ogura S I, Okura I. Water-soluble bis-(imida-zolylporphyrin) self-assemblies with large two-Photon absorption cross sections as potential agents for photodynamic therapy. J Med Chem, 2006, 49: 2276–2283

    Article  CAS  Google Scholar 

  19. Bhaskar A, Ramakrishna G, Lu Z K, Twieg R, Hales J M, Hagan D J, Stryland E V, Goodson T III. Investigation of two-photon absorption properties in branched alkene and alkyne chromohhores. J Am Chem Soc, 2006, 128: 11840–11849

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. Balema V P, Wiench J W, Pruski M, Pecharsky V K. Mechanically induced solid-State generation of Phosphorus ylides and the solvent-free wittig reaction. J Am Chem Soc, 2002, 124: 6244–6245

    Article  CAS  Google Scholar 

  22. Ren Y, Fang Q, Yu W T, Lei H, Tian Y P, Jiang M H, Yang Q C, Thomas C K M. Synthesis, structures and two-photon pumped up-conversion lasing properties of two new organic salts. J Mater Chem, 2000, 10: 2025–2030

    Article  CAS  Google Scholar 

  23. Wang C K, Zhao K, Su Y, Ren Y, Zhao X, Luo Y. Solvent effects on the electronic structure of a newly synthesized two-photon polymerization initiator. J Chem Phys, 2003, 119: 1208–1213

    Article  CAS  Google Scholar 

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Supported by the National Natural Science Foundation of China (Grant Nos. 50532030, 50703001 & 20771001), the National Natural Science Foundation of Anhui Province (Grant No. 070414188), Doctoral Program Foundation of the Ministry of Education of China, Education Committee of Anhui Province (Grant No. 2006KJ032A & KJ2009A52), Team for Scientific Innovation Foundation of Anhui Province (Grant No. 2006KJ007TD), Young Teacher Foundation of Institution of High Education of Anhui Province (Grant No. 2007jq1019), Ministry of Education and Person with Ability Foundation of Anhui University

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Gan, X., Zhou, H., Shi, P. et al. A new series of two-photon polymerization initiators: Synthesis and nonlinear optical properties. Sci. China Ser. B-Chem. 52, 2180–2185 (2009). https://doi.org/10.1007/s11426-009-0276-8

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  • DOI: https://doi.org/10.1007/s11426-009-0276-8

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