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Fluorine-Mediated Benzothiadiazole Derivatives for Second-Order Nonlinear Optics

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Abstract

With increasing research interests in the field of light-matter interactions, various methods have been developed for regulating nonlinear optical (NLO) materials. However, the design and synthesis of organic molecular materials for second-order nonlinear optics remain a great challenge because of the strict requirement of the materials to possess a noncentrosymmetric structure. In this work, two benzothiadiazole (BTD) derivatives referred to as BTD-H and BTD-F were synthesized, and their NLO properties in the crystalline states were studied. It was found that introducing fluorine into the BTD backbone effectively tuned the crystal packing styles of BTD derivatives to a noncentrosymmetric system for effective second-order NLO responses. Such a strategy to induce the noncentrosymmetric structure by introducing the fluorine atoms and halogen interactions may provide guidance for future engineering of organic NLO molecular materials.

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References

  1. Yu Balakina M, Nefediev SE (2006) Solvent effect on geometry and nonlinear optical response of conjugated organic molecules. Int J Quantum Chem 106(10):2245–2253

    Article  Google Scholar 

  2. Blouin N, Michaud A, Leclerc M (2007) A low-bandgap poly(2,7-carbazole) derivative for use in high-performance solar cells. Adv Mater 19(17):2295–2300

    Article  Google Scholar 

  3. Champagne B, Kirtman B (2001) Theoretical approach to the design of organic molecular and polymeric nonlinear optical materials. In: Nalwa HS (ed) Handbook of Advanced Electronic and Photonic Materials and Devices. Elsevier, Amsterdam, pp 63–126. https://doi.org/10.1016/b978-012513745-4/50073-1

    Chapter  Google Scholar 

  4. Kelderman E, Starmans WAJ, van Duynhoven JPM et al (1994) Triphenylcarbinol derivatives as molecules for second-order nonlinear optics. Chem Mater 6(4):412–417

    Article  Google Scholar 

  5. Torrent-Sucarrat M, Solà M, Duran M et al (2004) Basis set and electron correlation effects on initial convergence for vibrational nonlinear optical properties of conjugated organic molecules. J Chem Phys 120(14):6346–6355

    Article  Google Scholar 

  6. Kato SI, Matsumoto T, Ishi-I T et al (2004) Strongly red-fluorescent novel donor–π-bridge–acceptor–π-bridge–donor (D–π–A–π–D) type 2, 1, 3-benzothiadiazoles with enhanced two-photon absorption cross-sections. Chem Commun 20:2342–2343

    Article  Google Scholar 

  7. Loboda O, Zaleśny R, Avramopoulos A et al (2009) Linear and nonlinear optical properties of [60]fullerene derivatives. J Phys Chem A 113(6):1159–1170

    Article  Google Scholar 

  8. Li M, Zhang H, Zhang Y et al (2016) Facile synthesis of benzothiadiazole-based chromophores for enhanced performance of second-order nonlinear optical materials. J Mater Chem C 4(38):9094–9102

    Article  Google Scholar 

  9. Wang JL, Xiao Q, Pei J (2010) Benzothiadiazole-based d–π-a–π-D organic dyes with tunable band gap: synthesis and photophysical properties. Org Lett 12(18):4164–4167

    Article  Google Scholar 

  10. Jiang D, Chen SH, Xue Z et al (2016) Donor–acceptor molecules based on benzothiadiazole: synthesis, X-ray crystal structures, linear and third-order nonlinear optical properties. Dye Pigment 125:100–105

    Article  Google Scholar 

  11. Han X, Gong WX, Tong Y et al (2017) Synthesis and properties of benzothiadiazole-pyridine system: the modulation of optical feature. Dye Pigment 137:135–142

    Article  Google Scholar 

  12. Gómez SL, Lenart VM, Turchiello RF et al (2016) Nonlinear optical properties of dye-doped E7 liquid crystals at the nematic–isotropic transition. Liq Cryst 43(2):268–275

    Article  Google Scholar 

  13. Chen SH, Li YJ, Yang WL et al (2010) Synthesis and tuning optical nonlinear properties of molecular crystals of benzothiadiazole. J Phys Chem C 114(35):15109–15115

    Article  Google Scholar 

  14. Zhang XY, Xu YY, Giordano F et al (2016) Molecular engineering of potent sensitizers for very efficient light harvesting in thin-film solid-state dye-sensitized solar cells. J Am Chem Soc 138(34):10742–10745

    Article  Google Scholar 

  15. Nguyen TL, Choi H, Ko SJ et al (2014) Semi-crystalline photovoltaic polymers with efficiency exceeding 9% in a ~ 300 nm thick conventional single-cell device. Energy Environ Sci 7(9):3040–3051

    Article  Google Scholar 

  16. Kim J, Yun MH, Kim GH et al (2014) Synthesis of PCDTBT-based fluorinated polymers for high open-circuit voltage in organic photovoltaics: towards an understanding of relationships between polymer energy levels engineering and ideal morphology control. ACS Appl Mater Interfaces 6(10):7523–7534

    Article  Google Scholar 

  17. Anant P, Lucas NT, Jacob J (2008) A simple route toward the synthesis of bisbenzothiadiazole derivatives. Org Lett 10(24):5533–5536

    Article  Google Scholar 

  18. Chen CT (2004) Evolution of red organic light-emitting diodes: materials and devices. Chem Mater 16(23):4389–4400

    Article  Google Scholar 

  19. Friend RH, Gymer RW, Holmes AB et al (1999) Electroluminescence in conjugated polymers. Nature 397(6715):121–128

    Article  Google Scholar 

  20. Jenekhe SA, Osaheni JA (1994) Excimers and exciplexes of conjugated polymers. Science 265(5173):765–768

    Article  Google Scholar 

  21. Duan YL, Ju CG, Yang G et al (2016) Aggregation induced enhancement of linear and nonlinear optical emission from a hexaphenylene derivative. Adv Funct Mater 26(48):8968–8977

    Article  Google Scholar 

  22. Xu JL, Semin S, Cremers J et al (2015) Controlling microsized polymorphic architectures with distinct linear and nonlinear optical properties. Adv Opt Mater 3(7):948–956

    Article  Google Scholar 

  23. Xu JL, Semin S, Niedzialek D et al (2013) Self-assembled organic microfibers for nonlinear optics. Adv Mater 25(14):2084–2089

    Article  Google Scholar 

  24. Xu JL, Semin S, Rasing T et al (2015) Organized chromophoric assemblies for nonlinear optical materials: towards (sub)wavelength scale architectures. Small 11(9–10):1113–1129

    Article  Google Scholar 

  25. Yuan CQ, Li XY, Semin S et al (2018) Chiral lead halide perovskite nanowires for second-order nonlinear optics. Nano Lett 18(9):5411–5417

    Article  Google Scholar 

  26. Mutailipu M, Zhang M, Yang Z et al (2019) Targeting the next generation of deep-ultraviolet nonlinear optical materials: expanding from borates to borate fluorides to fluorooxoborates. Acc Chem Res 52(3):791–801

    Article  Google Scholar 

  27. Mutailipu M, Zhang M, Zhang B et al (2018) SrB5O7F3 functionalized with [B5O9F3]6− chromophores: accelerating the rational design of deep-ultraviolet nonlinear optical materials. Angew Chem Int Ed Engl 57(21):6095–6099

    Article  Google Scholar 

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Acknowledgements

This study was supported by China International Science and Technology Project (No. 2016YFE0114900), and National Natural Science Foundation of China (No. 21761132007).

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Author notes

  1. Huina You and Qinqin Xu have contributed equally to this work.

Authors and Affiliations

  1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300350, China

    Huina You, Qinqin Xu, Chenggong Ju, Yaqing Feng & Bao Zhang

  2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin, 300072, China

    Yaqing Feng

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  1. Huina You
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  2. Qinqin Xu
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  3. Chenggong Ju
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  4. Yaqing Feng
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  5. Bao Zhang
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Corresponding author

Correspondence to Bao Zhang.

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You, H., Xu, Q., Ju, C. et al. Fluorine-Mediated Benzothiadiazole Derivatives for Second-Order Nonlinear Optics. Trans. Tianjin Univ. 25, 603–610 (2019). https://doi.org/10.1007/s12209-019-00211-0

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  • DOI: https://doi.org/10.1007/s12209-019-00211-0

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