Weak Interaction-Based Organic Luminescent Materials

doi:10.6023/cjoc202404041

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2453-2468.DOI: 10.6023/cjoc202404041 Previous Articles Next Articles

REVIEWS

弱作用基有机发光材料

沈钇灼^a, 罗康为^a, 徐清洋^a^,^b^,^c, 张鉴予^d, 孙景志^a^,^c, 张浩可^a^,^b^,^c^,^*(), 唐本忠^a^,^e^,^*()

a 浙江大学高分子科学与工程学系高分子合成与功能构造教育部重点实验室杭州 310058
b 浙江大学杭州国际科创中心浙江-以色列自组装功能材料联合实验室杭州 311215
c 浙江大学绍兴研究院生命健康研究中心大健康材料分中心浙江绍兴 312000
d 格罗宁根大学 Stratingh化学研究所格罗宁根 9747 AG 荷兰
e 香港中文大学(深圳)理工学院深圳分子聚集体科学与工程研究院广东深圳 518172

收稿日期:2024-04-29 修回日期:2024-05-30 发布日期:2024-06-24
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(22205197); 浙江大学大学生科研训练(X2023349)

Weak Interaction-Based Organic Luminescent Materials

Yizhuo Shen^a, Kangwei Luo^a, Qingyang Xu^a^,^b^,^c, Jianyu Zhang^d, JingZhi Sun^a^,^c, Haoke Zhang^a^,^b^,^c(), BenZhong Tang^a^,^e()

a MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310058
b Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials, ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311215
c Centre of Healthcare Materials, Shaoxing Institute, Zhejiang University, Shaoxing, Zhejiang 312000
d Stratingh Institute for Chemistry, University of Groningen, 9747 AG Groningen, The Netherlands
e School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong, Shenzhen (CUHK-Shenzhen), Guangdong 518172

Received:2024-04-29 Revised:2024-05-30 Published:2024-06-24
Contact: *E-mail: zhanghaoke@zju.edu.cn; tangbenz@cuhk.edu.cn
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22205197); Student Research Training Program of Zhejiang University(X2023349)

In recent years, the abnormal luminescent phenomena discovered in non-conjugated structures or even lacking π-electrons have drawn widespread attention. However, due to unclear luminescent mechanisms and poor luminescent performance, the development in this field has been relatively slow. In this review, the latest research progress in the through-space conjugation (TSC) mechanism and performance regulation of weak interaction-based luminescent materials in recent years is summarized. Firstly, based on the mechanism research model of non-conjugated multiarylalkanes, the TSC mechanism of weak interaction-based luminescent materials is proposed. Strategies have been developed for regulating TSC intensity by changing the conformation of molecules and the electronic structure of subunits, leading to the successful development of weak interaction-based luminescent polymers with highly efficient full-color emission. Meanwhile, it is found that TSC widely exists in twisted molecules with π-conjugated structure, believed to be an important luminescent mechanism for aggregation-induced emission effect.

Key words: through-space conjugation, weak interaction, fluorescence, multiarylalkanes, aggregation-induced emission

Cite this article

Yizhuo Shen, Kangwei Luo, Qingyang Xu, Jianyu Zhang, JingZhi Sun, Haoke Zhang, BenZhong Tang. Weak Interaction-Based Organic Luminescent Materials[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2453-2468.

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Fig. & Tab. 14

Figure 1. Mechanism schematic diagram of through-bond and through-space conjugation

Figure 2. (a) Structures of the oligomers containing diphenylmethane units, and (b) non-linear relationship between TSC strength and molecular length in oligomers[67]

Figure 3. PL spectra (a~c) of three DPM derivatives under different water fractions; (d) Isosurface plots of the interaction region indicator function for the optimized excited-state conformation; (e) Comparison of structural parameters[68]

Figure 4. (a) Chemical and crystal structures of three isomers of tri(biphenyl)methane; (b) Solid-state PL spectra of p-TBPM, (c) m-TBPM, and (d) o-TBPM under different excitations[73]

Figure 5. (a) PL spectra of 222-TNM, (b) 122-TNM, (c) 112-TNM, and (d) 111-TNM at different water fractions in acetonitrile/water mixtures; (e) Trends in intermolecular and intramolecular interactions as well as TSC strength changes for the four constitutional isomers; (f) Trends in the luminescent properties and rigidity of aggregates for the four molecules[75]

Figure 6. Odd-even effect of alkyl chain length on TSC strength in tetraphenylalkanes[77]

Figure 7. (a) Absorption spectra of C3-TPA, Me-C3-TPA, and Ph-C3-TPA in solution; Solid-state emission spectra of (b) C3-TPA, (c) Me-C3-TPA, and (d) Ph-C3-TPA at variable excitation wavelengths[79]

Figure 8. Enhancing TSC in triphenylmethane by introducing electron-withdrawing groups on the phenyl rings[81]

Figure 9. (a~b) PL spectra of DMA-CN-DPM and (e~f) DMA-CN-BP in acetonitrile/water mixed solvent as a function of increasing water fraction, along with trend graphs showing the variation of emission wavelength and intensity with different water fraction. Trend graph showing the emission peak variation of (c) DMA-CN-DPM and (g) DMA-CN-BP in different polar solvents. Temperature-dependent PL spectra of (d) DMA-CN-DPM and (h) DMA-CN-BP[88]

Figure 10. (a) Schematic diagram of the multiple emission mechanism of TPMI-X; Solid-state PL spectra of (b) TPMI-Cl, (c) TPMI-Br, and (d) TPMI-I under variable excitation wavelengths[89]

Figure 11. PL spectra of (a,b) An-MO-PR and (c,d) Bn-MO-PR in (a,c) high-concentration solution and (b,d) in the solid state under variable excitation wavelengths[90]

Figure 12. PL spectra of PDPM in a 1 mol/L THF solution using (a) standard detector and (b) near-infrared detector under variable excitation wavelengths; (c) fluorescence images of PDPM at varying concentrations and excitation wavelengths; (d) EPR spectrum of PDPM at different concentrations[98]

Figure 13. TSC-based luminescence mechanism of tetraphenylethylene (TPE)[101]

Figure 14. (a) Chemical structures and conformational parameters of the isomers p-TPh, m-TPh, and o-TPh in single-crystal state; (b) Absorption spectra of the isomeric triphenylbenzenes in solution state and PL spectra in DMF/water mixtures; (c) Computational analysis of the excited-state electronic structure and TSC-based luminescence mechanism for the isomeric triphenylbenzenes[103]

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弱作用基有机发光材料

Weak Interaction-Based Organic Luminescent Materials

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