多芳基烷烃中的空间共轭

doi:10.6023/cjoc202505015

有机化学 ›› 2025, Vol. 45 ›› Issue (11): 4037-4047.DOI: 10.6023/cjoc202505015 上一篇下一篇

综述与进展

多芳基烷烃中的空间共轭

吴家杰^a^,^b^,^c^,^d^,^†, 朱宸^b^,^†, 王毅朴^e^,^*(), 杨永珍^a^,^*(), 张浩可^b^,^c^,^d^,^*()

^a 太原理工大学新材料界面科学与工程教育部重点实验室太原 030024
^b 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高分子合成与功能构造教育部重点实验室杭州 310058
^c 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浙江-以色列自组装功能材料联合实验室杭州 311215
^d 浙江大学经血管植入器械全国重点实验室经血管植入器械全国重点实验室杭州 310009
^e 南通大学化学化工学院南通 226019

收稿日期:2025-05-12 修回日期:2025-06-12 发布日期:2025-08-18
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(22205197)

Through-Space Conjugation in Multiarylalkanes

Jiajie Wu^a^,^b^,^c^,^d, Chen Zhu^b, Yipu Wang^e^,^*(), Yongzhen Yang^a^,^*(), Haoke Zhang^b^,^c^,^d^,^*()

^a Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, Taiyuan University of Technology, Taiyuan 030024
^b MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310058
^c Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials, ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311215
^d State Key Laboratory of Transvascular Implantation Devices, Zhejiang University, Hangzhou 310009
^e School of Chemistry and Chemical Engineering, Nantong University, Nantong 226019

Received:2025-05-12 Revised:2025-06-12 Published:2025-08-18
Contact: *E-mail: wangyipu@ntu.edu.cn; yyztyut@126.com; zhanghaoke@zju.edu.cn
About author:
^†These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22205197)

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摘要/Abstract

有机发光材料在现代科技领域具有重要的应用价值. 近些年发现的弱作用基发光材料(如多芳基烷烃)突破了传统发光材料基于π共轭理论设计框架. 研究表明, 这类材料通过空间共轭产生发光, 其中π-π、n-π和n-n等多种空间共轭相互作用共同调控发光性能. 由于多芳基烷烃小分子具有结构清晰和容易修饰的优势, 因此本文主要从构象调控、D-A电子结构调控以及n电子结构调控三个方面系统总结了多芳基烷烃小分子中的空间共轭机制. 通过对其发光机理的研究发现, 构象调控和D-A电子结构主要通过π-π空间共轭影响其发光; 而n电子结构调控则利用N原子上的孤对电子引入新n-π和n-n空间共轭, 从而实现了更长波长的发射和较高的发光效率. 通过对多芳基烷烃小分子的空间共轭总结, 不仅完善了现有的空间共轭发光机制, 更为设计新型高效弱作用基发光材料提供了重要指导.

关键词: 荧光, 空间共轭, 多芳基烷烃, 有机发光材料

Organic luminescent materials hold significant promise for applications in modern technology. Traditionally, their design has been guided by π-conjugation theory. However, the recent discovery of weak interactions-based luminescent materials, such as multiarylalkanes (MAAs), has challenged this paradigm. Emerging research suggests that these materials emit light from through-space conjugation (TSC), including π-π, n-π, and n-n TSC. Owing to their well-defined structures and facile chemical modification, MAAs serve as ideal models for investigating TSC. This review systematically examines the mechanisms of TSC in these systems from three key perspectives: conformational regulation, donor-acceptor (D-A) and n-electronic modulation. Studies on their photophysical processes reveal that conformational control and D-A electronic modulation predominantly influence emission through π-π TSC. In contrast, tuning the n-electron structure, particularly involving lone pair electrons on nitrogen atoms, introduces n-π and n-n TSC, enabling red-shifted emission and enhanced luminescence efficiency. By providing a comprehensive analysis of TSC in MAAs, this review refines the current understanding of TSC-based luminescence and offers valuable design principles for developing novel, highly efficient, weak interactions-based luminescent materials.

Key words: fluorescence, through-space conjugation, multiarylalkanes, organic luminescent materials

引用此文

吴家杰, 朱宸, 王毅朴, 杨永珍, 张浩可. 多芳基烷烃中的空间共轭[J]. 有机化学, 2025, 45(11): 4037-4047.

Jiajie Wu, Chen Zhu, Yipu Wang, Yongzhen Yang, Haoke Zhang. Through-Space Conjugation in Multiarylalkanes[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4037-4047.

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图/表 9

Figure 1. (a) Structures and luminescent photographs of PPM, PMPM and PTMPM in film and solution; (b) Structures and solid-state PL spectra of OPM[2]-OPM[7] under different excitation wavelength (λex) (a) Reproduced from Ref. [37], copyright 2017 John Wiley and Sons; (b) Reproduced from Ref. [38], copyright 2024 John Wiley and Sons.

Figure 2. PL spectra of (a) OMe-CN-DPM and (b) DM-CN-DPM in acetonitrile and water mixtures with different water fractions (fw); (c) HOMO and LUMO of DPM, OMe-CN-DPM and DM-CN-DPM in the optimized excited states Reproduced from Ref. [40], copyright 2024 Springer Nature.

Figure 3. PL spectra of (a) o-1Py-1Ph, (b) o-2Py, and (c) o-2Md in the bulky state with different excitation wavelengths; (d) Schematic illustration of the excited-state decay pathways of these three samples Reproduced from Ref. [41], copyright 2025 Elsevier.

Figure 4. PL spectra of (a) o-TBPM, (b) m-TBPM, and (c) p-TBPM in the solid state with different excitation wavelengths; Reorganization energy of (d) o-TBPM, (e) m-TBPM, and (f) p-TBPM in the gas phase; (g) Single crystal structures Reproduced from Ref. [45], copyright 2024 Springer Nature.

Figure 5. Solid-state PL spectra of (a) 222-TNM, (b) 122-TNM, (c) 112-TNM, and (d) 111-TNM with different excitation wavelengths; (e) Root-mean-square deviation (RMSD) calculations of these four isomers in the gas phase; (f) The intermolecular interaction analysis by the CrystalExplorer, and the schematic illustration of the influence of intra-/intermolecular interactions on the RSC strength Reproduced from Ref. [46], copyright 2024 Springer Nature.

Figure 6. Solid-state PL spectra of (a) TPM, (b) TPM-MO, (c) TPM-DMA, and (d) 111-TNM; (e) Electronic static potential mapped on the isosurface of electronic density, experimental luminescence quantum yield and calculated energy gap Reproduced from Ref. [47], copyright 2021 American Chemical Society.

Figure 8. Solid-state PL spectra of (a) o-4Py, (b) p-4Py crystal under different excitation wavelengths (λex); (c) Distribution of electron cloud and energy gap (ΔE) for o-4Py(1), o-4Py(2), o-4Py(3), and p-4Py with 4 nitrogen atoms in different positions of the optimized excited-state conformation Reproduced from Ref. [41], copyright 2025 Elsevier

Figure 9. (a) Molecular structures and solid-state fluorescence images of C1-TPA to C7-TPA; (b) RMSD plot of TPAs with varying alkyl chain lengths; (c) Intramolecular staggered and face-to-face packing structures of C2-TPA to C5-TPA; (d) Schematic illustration of the switching between different photophysical processes associated with the excited-state odd-even effect Reproduced from Ref. [53], copyright 2023 American Chemical Society

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多芳基烷烃中的空间共轭

Through-Space Conjugation in Multiarylalkanes

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