Through-Space Conjugation in Multiarylalkanes

doi:10.6023/cjoc202505015

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (11): 4037-4047.DOI: 10.6023/cjoc202505015 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 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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