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| 題名: | Deep-red carbazole–furanonitrile emitters with linker-dependent planarity and aggregation-induced emission |
| 作者: | Liu, Shih-Fan;Hsieh, Chung-Hung;Thomas, K. R. Justin;Chen, Chih-Hsin |
| 日期: | 2025-10-09 |
| 上傳時間: | 2026-04-16 12:05:29 (UTC+8) |
| 摘要: | Deep-red emitters have attracted considerable attention in the biomedical field owing to their strong tissue penetration, good biocompatibility, and potential to promote cellular activation and repair. However, many deep-red molecules suffer from low photoluminescence quantum yields (PLQYs) due to dipole–dipole quenching, which limits their performance. To address this, we employed an aggregation-induced emission (AIE) strategy, which offers high brightness, large Stokes shifts, and resistance to aggregation-caused quenching (ACQ). Four donor–acceptor (D–A)- type compounds (5a–5d) were synthesized, featuring carbazole as the electron donor, which enhances molecular rigidity by restricting bond rotation, and 2-oxo-4-phenyl-2,5-dihydrofuran-3-carbonitrile as the electron acceptor to achieve red-shifted emission. The four molecules differ in their π-conjugated linkers, enabling investigation of the effect of molecular planarity on photophysical properties. In solution, their maximum emission wavelengths were 535.0, 638.4, 652.0, and 643.0 nm, respectively, while in thin films, 5a–5c exhibited further red shifts to 654, 699, and 738 nm. Among them, 5a showed the highest fluorescence intensity under UV excitation in the solid state. All compounds displayed twisted intramolecular charge transfer (TICT) behavior in high-polarity solvents, and AIE measurements revealed that only 5a and 5c possessed distinct AIE characteristics. Single-crystal analyses of 5a and 5b indicated that AIE activity correlates with the dihedral angle between the carbazole and the adjacent aromatic ring; larger dihedral angles reduce π–π stacking upon aggregation and restrict intramolecular bond rotation, thereby promoting AIE. These results provide valuable structural insight for the rational design of high-performance AIE-active deep-red emitters for biomedical and optoelectronic applications. |
| 關聯: | Journal of the Chinese Chemical Society 72(10) , p. 1171-1182 |
| DOI: | 10.1002/jccs.70111 |
| 顯示於類別: | [化學學系暨研究所] 期刊論文
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