窄化芘基发光分子半峰宽的合成策略

doi:10.6023/cjoc202403054

有机化学 ›› 2024, Vol. 44 ›› Issue (8): 2504-2512.DOI: 10.6023/cjoc202403054 上一篇下一篇

研究论文

窄化芘基发光分子半峰宽的合成策略

谢志鑫^a, 黎少玲^a, 刘威^a, 严楷^a(), 蒋涛^a, 刘一苇^a, Md. Monarul Islam^a^,^*(), 冯星^a^,^*()

a 广东工业大学材料与能源学院 510006
b 广东工业大学分析测试中心 510006
c 孟加拉国科学和工业研究理事会(BCSIR)化学研究部达卡-1205丹蒙迪孟加拉国

收稿日期:2024-05-14 修回日期:2024-06-22 发布日期:2024-07-02
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(21975054); 广东省基础与应用基础研究基金(2020A1515110992)

An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters

Zhixin Xie^a, Shaoling Li^a, Wei Liu^a, Kai Yan^a(), Tao Jiang^a, Yiwei Liu^a, Md. Monarul Islam^a(), Xing Feng^a()

a School of Materials and Energy, Guangdong University of Technology, Guangzhou 510006
b Analysis and Test Center, Guangdong University of Technology, Guangzhou 510006
c Synthesis Laboratory, Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka-1205, Bangladesh

Received:2024-05-14 Revised:2024-06-22 Published:2024-07-02
Contact: *E-mail: atc_yank@gdut.edu.cn; mmipavel@yahoo.com; hyxhn@sina.com
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21975054); Guangdong Basic and Applied Basic Research Foundation(2020A1515110992)

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摘要/Abstract

开发高效窄带发射的有机发光材料是实现有机发光二极管高色纯度、高分辨的关键. 针对有机发光分子的发射光谱谱较宽的问题, 基于芘基发光材料体系, 提出了利用空间立体效应窄化发光分子的半峰宽的分子设计策略. 利用空间位阻效应, 通过在芘的2-位引入大位阻的取代基团, 降低了3-位取代基团三苯胺的分子转动, 设计合成的芘基发光分子5具有相对高的固态量子产率(>0.31)和固态下较窄的半峰宽(相较于溶液态和没有立体效应存在下). 特别的, 制备的化合物5c在固态下显示出最大的发射峰位于484 nm, 量子产率较高(0.38)和发射半峰宽较窄(49 nm).

关键词: 聚集诱导发光, 芘, 窄带发射, 立体效应

The construction of high color purity and high resolution organic light-emitting diodes (OLEDs) is facilitated by the development of highly-efficient organic luminescent materials with narrow-band emission. Herein, in order to address the problem of broad emission spectra of organic luminescent materials, an effective molecular design strategy is presented to reduce the full width at half maximum (FWHM) of emission by integrating the steric hindrance effect in the pyrene system. As the bulky group was introduced into the 2-position, compounds 5 not only show a relative high quantum yield (>0.31) in the solid state, but also can suppress the molecular rotation of triphenylamine (TPA) at the 3-position to narrow the FWHM in the solid state compared to that in solution. Compound 5c containing biphenyl units exhibits a maximum emission peak at 484 nm with a quantum yield of 0.38 and FWHM value of 49 nm in the solid state.

Key words: aggregation-induced emission, pyrene, narrow-band emission, steric effect

引用此文

谢志鑫, 黎少玲, 刘威, 严楷, 蒋涛, 刘一苇, Md. Monarul Islam, 冯星. 窄化芘基发光分子半峰宽的合成策略[J]. 有机化学, 2024, 44(8): 2504-2512.

Zhixin Xie, Shaoling Li, Wei Liu, Kai Yan, Tao Jiang, Yiwei Liu, Md. Monarul Islam, Xing Feng. An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2504-2512.

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图/表 5

Scheme 1. Synthetic route for target compounds 5a~5d

Figure 1. Computed molecular orbital plots (B3LYP/6-31G*) of 5a~5d

Compd.	ε_max/(L•mol^－1•cm^－1)	λ_max,PL/nm	τ/ns	Φ_f	α(AIE)^d	k_r^e/(10⁷ s^－1)	k_nr^f/(10⁷ s^－1)	FWHM/nm
5a	118379	505^a 490^b 477^c	5.05^a 9.28^b 3.35^c	0.53^a 0.19^b 0.31^c	0.58	10.49^a 2.04^b 9.25^c	9.31^a 8.73^b 20.60^c	84^a 68^b 57^c
5b	66312	475^a 476^b 483^c	1.02^a 2.18^b 2.41^c	0.01^a 0.37^b 0.50^c	50	0.98^a 16.97^b 20.74^c	97.05^a 28.90^b 20.75^c	81^a 79^c 76^c
5c	77805	469^a 464^b 484^c	2.64^a 2.01^b 2.57^c	0.64^a 0.31^b 0.38^c	0.59	24.24^a 15.42^b 14.78^c	13.63^a 34.33^b 24.11^c	67^a 57^b 49^c
5d	42776	502^a 507^b 512^c	3.81^a 2.85^b 4.61^c	0.69^a 0.09^b 0.32^c	0.46	18.11^a 3.15^b 6.94^c	8.13^a 31.93^b 14.75^c	106^a 82^b 68^c

Table 1. Photophysical properties of compounds 5a~5d

Figure 2. (A) UV-vis absorption spectra and (B) emission spectra of compounds 5 in THF (10－5 mol/L) at room temperature; (C) emission spectra of compounds 5 in the solid state; (D) quantum yields of compounds 5 in THF/H2O mixtures with water fractions (fw) of 0 (black), fw=99% (red) and in the solid state (blue); (E) fluorescence spectra of compound 5d recorded in six solvents at (ca. 10-5 mol/L); (F) plots of Stokes shift (?ν) vs ?f(ε,n) of compounds 5a~5d

Figure 3. (A) Emission spectra of 5b in THF/H2O mixtures with various water fractions (fw) (10－5 mol/L); (B) plot of the relative PL intensity I/I0 at different water fractions for 5b Inset: fluorescence images of 5b in THF/H2O mixtures at different fw (0 and 99%) values taken under 365 nm irradiation.

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窄化芘基发光分子半峰宽的合成策略

An Efficient Approach to Narrow the Emission Band of Pyrene-Based Emitters

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