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Current Organic Synthesis

Author(s): Kexiang Chen, Jiexue Wang*, Lu Li, Le Chang, Min Yang, Qihui Wang, Zhonghui Li and Guowei Deng*

DOI: 10.2174/1570179420666230330105047

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Synthesis and Characterization of a Julolidine-based Electro-optic Molecular Glass

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Abstract

Aim: Organic Electro-optic (EO) materials have recently gained considerable attention owing to their advantages compared to inorganic EO materials. Among different kinds of organic EO materials, organic EO molecular glass exhibits desired prospect because of its high chromophore loading density and large macroscopic EO activity.

Introduction: The objective of this study is to design and synthesize a novel organic EO molecular glass JMG utilizing julolidine moiety as the electron donor, thiophene moiety as the conjugated bridge, trifluoromethyl substituted tricyanofuran derivate (Ph-CF3-TCF) as the electron acceptor.

Methods: The JMG’s structure was characterized through NMR and HRMS. The photophysical property, glass transition temperature, first hyperpolarizability (β) and dipole moment (μ) of JMG were determined through UV-vis spectra, DSC test and DFT calculation.

Results: JMG’s Tg reached to 79°C and it can form high-quality optical film. The theoretical calculation shows that the first hyperpolarizability (β) and dipole moment (μ) of JMG were calculated to 730×10-30 esu and 21.898 D. After connecting poling with the poling voltage of 49 V/μm at 90℃ for 10 min, the highest EO coefficient (r33) of the poled JMG films reached to 147 pm/V.

Conclusion: A novel julolidine-based NLO chromophore with two tert-butyldiphenylsilyl (TBDPS) groups was successfully prepared and characterized. TBDPS group is introduced as the film-forming group, and it also plays the role of isolation group, which can suppress the electrostatic interaction between chromophores, improve the poling efficiency and further enhance the EO activity. The excellent performances endow JMG with potential applications in device fabrication.

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