Optical Properties of Fluorinated Precursors to Porous Molecular Crystals

Date

2020-08

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Abstract

The effect of fluorination on the chemical and physical characteristics of organic porous materials is reviewed in Chapter 1. The fluorinated aromatic triazine discussed in Chapter 2 is a precursor to a porous molecular crystal. Its intramolecular rotations are flexible due to the repulsion between neighboring atoms of fluorine and nitrogen. Restriction of the intramolecular rotations by molecular aggregation can turn ON the fluorescence of the fluorinated aromatic triazine. Chapter 3 presents the fluorescence of the fluorinated aromatic triazine can also be turned ON by assembly after the addition of phthalic acid. The two carboxyl groups in phthalic acid can hold two molecules of fluorinated aromatic triazine close to each other, which restricted the intramolecular rotations of the fluorinated aromatic triazine and turned fluorescence on. In Chapter 4, a tetraphenylethylene grafted with fluorinated aromatics is described, which formed different solvated crystals with DMF and showed sensitive or inert response of solid-state fluorescence to DMF. In Chapter 5, the synthesis, spectra of absorption and emission in solution and aggregation, and photoreactions of five fluorinated tetraphenylethylene derivatives is presented.

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Keywords

fluorinated compounds, porous molecular crystals, aggregation-induced emission, dicarboxylic Acids, stimuli-responsive materials

Citation

Portions of this document appear in: Zhang, Zhenglin, Thien Lieu, Xiqu Wang, Olafs Daugulis, and Ognjen Š. Miljanić. "Synthesis and Optical Properties of Fluorinated Tetraphenylethylenes." ChemPhotoChem (2022): e202200011; and in: Zhang, Zhenglin, Mohamed I. Hashim, and Ognjen Š. Miljanić. "Aggregation-induced emission in precursors to porous molecular crystals." Chemical Communications 53, no. 72 (2017): 10022-10025; and in: Zhang, Zhenglin, Mohamed I. Hashim, Chia-Hua Wu, Judy I. Wu, and Ognjen Š. Miljanić. "Discrimination of dicarboxylic acids via assembly-induced emission." Chemical Communications 54, no. 82 (2018): 11578-11581; and in: Zhang, Zhenglin, Thien Lieu, Chia-Hua Wu, Xiqu Wang, Judy I. Wu, Olafs Daugulis, and Ognjen Š. Miljanić. "Solvation-dependent switching of solid-state luminescence of a fluorinated aromatic tetrapyrazole." Chemical Communications 55, no. 63 (2019): 9387-9390.