星型苯并菲-三嗪多刺激响应盘状液晶: 合成、性质与应用

doi:10.6023/A23010006

摘要/Abstract

盘状液晶作为有机光电功能材料具有学术研究价值和应用开发潜力. 通过Suzuki偶联反应合成了星型1,3,5-三嗪-苯并菲盘状液晶TPPTn (n=6, 8, 12). 化合物在溶液、薄膜与固体态都有良好的荧光发射, 具有聚集诱导效应, 有效克服了盘状分子聚集诱导荧光猝灭的弊端, 烷氧链长度的改变对化合物溶液、薄膜或固体的荧光性质影响相对较小. 重点研究的TPPT6呈现出由蓝到橙显著的溶致变色, 绝对量子产率最高可达43%; TPPT6在有机溶剂中呈现出较传统分子的升温猝灭不同的随温度升高荧光增强的温度刺激响应; TPPT6还具有明显的酸碱刺激响应, 核磁滴定证明质子化过程是导致酸致变色的关键; TPPTn系列化合物自组装呈矩形柱状中间相(Col_rec), 柱状相温度最宽达278 ℃, 三氟乙酸通过对三嗪离子化可调控TPPT的介晶行为. 此外, TPPT6可用于制备安全墨水以及绿光有机发光二极管. 该系列化合物在液晶半导体、荧光传感、信息加密和有机发光二极管等领域具有潜在的应用价值.

关键词: 苯并菲, 1,3,5-均三嗪, 多刺激响应, 盘状液晶, 聚集诱导效应, Suzuki-Miyaura交叉偶联

The electronic and optical properties of π-conjugated materials are determined by their molecular structures and supramolecular architectures. Discotic liquid crystals consist of π-conjugated aromatic core and peripheral alkyl chains, they self-organize into two-dimensional discotic columnar mesophase, which can be applied as charge carrier transport channel in optical and electronic thin-film devices. Order and dynamics are two unique features of discotic liquid crystalline semiconductors. Three star-shaped 1,3,5-triazine-triphenylene discotic liquid crystals TPPTn (n=6, 8, 12) were synthesized by Suzuki-Miyaura cross-coupling reaction and characterized. Thermogravimetric analysis (TGA) shows that TPPTn have good thermal stability, and their thermal decomposition temperatures were higher than 350 ℃. The ultraviolet-visible (UV-Vis) absorption spectra and fluorescence spectra showed that they have outstanding fluorescence emissions in solution, thin film and even in solid state, and the length of alkoxy chain affects a little the fluorescence properties of the film or solid state by affecting the molecular aggregation. TPPTn have the aggregation-induced emission (AIE) effect: longer the alkoxy chain, more obvious the AIE phenomenon, this AIE effectively overcomes the disadvantage of aggregation caused quenching (ACQ) of π-extended discotic liquid crystalline molecules. Further, TPPT6 exhibits significant solvatochromism from blue to orange with the increasing of solvent polarity, due to the intramolecular charge transfer (ICT), which provides possibility for visual recognition of solvent polarity. The fluorescent emission absolute quantum yield is up to 43%. What is more, TPPT6 exhibits a temperature-responsive fluorescence enhancement with increasing temperature in solution, which is different from the temperature quenching of traditional molecules, and the fluorescence exhibits a reversible switching from green to blue with increasing/decreasing of temperature. TPPT6 also has obvious acid-base stimuli- responsive fluorescent response by CF₃COOH and Et₃N. ¹H NMR titration proves that the protonation of triazine core is the mechanism to acid discoloration. Based on the acid-base stimuli response phenomena, two kinds of fluorescent safety inks have been designed and demonstrated. Differential scanning calorimetry (DSC), polarizing microscope (POM) and X-ray diffraction (XRD) indicate that these star-shaped molecules TPPTn have liquid crystal properties, self-organizing into columnar rectangular (Col_rec) mesophase with mesophase temperature range as wide as 278 ℃. Trifluoroacetic acid (CF₃COOH) modulates successfully the mesomorphic behavior of TPPTn by ionizing the triazine core. In addition, TPPT6 also displays electroluminescent properties, which has been applied to a green organic light-emitting diode (OLED), and the luminous efficiency of OLED reaches 7.41 lm/W. The star-shaped triphenylene-triazine TPPTn have potential applications as liquid crystalline semiconductors, fluorescence sensing, information encryption and organic light-emitting diodes.

Key words: triphenylene, triazine, multi-stimuli response, discotic liquid crystals, aggregation-induced emission, Suzuki- Miyaura cross-coupling reaction

引用此文

曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, Donnio Bertrand. 星型苯并菲-三嗪多刺激响应盘状液晶: 合成、性质与应用[J]. 化学学报, 2023, 81(5): 469-479.

Zeng Chongyang, Hu Ping, Wang Biqin, Fang Wenyan, Zhao Keqing, Donnio Bertrand. Star-shaped Triphenylene-triazine Multi-stimuli Responsive Discotic Liquid Crystals: Synthesis, Properties and Applications[J]. Acta Chimica Sinica, 2023, 81(5): 469-479.

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图/表 14

图式1. 星型化合物苯并菲-苯-三嗪TPPTn: 分子结构、命名、合成与收率

Scheme 1. Star-shaped compounds triphenylene-phenyl-triazine TPPTn: molecular structure, nomenclature, synthesis and yield

图1. TPPT6/8/12在THF中的紫外-吸收光谱(a); 化合物荧光发光光谱(b); 不同状态下TPPTn的荧光照片(c); TPPT1前线轨道电子云分布(d)

Figure 1. UV-Vis absorption spectra of TPPT6/8/12 in THF (a); fluorescent emission spectra (b); fluorescence photos of TPPTn in various states (c); electron distribution on frontier molecular orbitals of TPPT1 (d)

图2. TPPT6在不同溶剂中的紫外-可见吸收光谱(a); 荧光发射光谱(b)和Lippert-Mataga曲线(c), 插入图片为荧光照片(从左往右极性增大)

Figure 2. UV-Vis absorption spectra (a); fluorescence emission spectra (b) and Lippert-Mataga curve (c) of TPPT6 in different solvents, and inserted image is fluorescence photos (polarity increases from left to right)

Compound	Solvent	λ_a	ε (×10⁴)	λ_e	QY/%	Δν
TPPT6	CHX	360	19.62	449	43.02	5506
	toluene	362	21.27	454	42.20	5597
	EA	364	9.41	478	22.02	6552
	THF	364	24.89	490	18.44	7064
	EtOH	367	21.31	519	9.59	7980
	DMF	368	22.16	548	0.96	8925

表1. TPPT6的光物理参数

Table 1. Photophysical property parameters of TPPT6

图3. TPPT6在不同含水量的THF/H2O溶液中的吸收光谱(a), 发射光谱(b)与荧光强度变化图(c), 插入图片为聚集诱导荧光照片; (d)为含水量0~10%间的荧光光谱, 插入图片为荧光猝灭拟合曲线

Figure 3. The UV-Vis absorption spectra (a), PL emission spectra (b) and fluorescence intensity change map (c) of TPPT6 in THF/H2O with different water fraction. (d) for the water fraction between 0~10% of the fluorescence spectra, inserted picture for the fluorescence quenching fitting curve

图4. TPPT6在乙酸乙酯中加热前后的紫外-可见吸收和荧光光谱(a); 交替加热-冷却的波长变化图(b); 在25~75 ℃范围内的荧光光谱(c), 插入图片为温度与I/I0的线性拟合图; (d)为300 K与350 K的TPPT构象

Figure 4. UV-Vis absorption and fluorescence spectra of TPPT6 in lower and higher temperature in CH3COOEt (a); fluorescence wavelength variation with alternating heating-cooling (b); fluorescence spectra at 25~75 ℃ (c), insert the picture for the linear fitting of temperature and I/I0; (d) the TPPT molecular conformations at 300 K and 350 K

图5. TPPT6的三氯甲烷溶液在TFA/TEA酸碱刺激过程中的紫外-可见吸收光谱(a); 荧光-周期循环图(b); 发射光谱(c); 固体酸碱刺激前后的荧光光谱(d); 固体(e)的日光/荧光照片和薄膜(f)的荧光照片

Figure 5. Photophysical property of TPPT6 by acid-base (CF3COOH/Et3N) stimulation. UV-Vis absorption spectra (a); fluorescence periodic cycle diagram (b); emission spectra (c); solid sample fluorescence spectra before and after acid-base stimulation (d); sunlight/fluorescence images of solid samples (e); fluorescence images of thin films (f)

Compd.	2nd heating [1st cooling]/℃ (∆H/(kJ•mol^-1))
TPPT6	Col_rec 278 (36.26) I [I 263 (38.85) Col_rec]
TPPT8	Col_rec 231 (27.90) I [I 221 (29.40) Col_rec]
TPPT12	Cr -7 Col_rec 149 (12.19) I [I 153 (14.94) Col_rec -13 Cr]
TPPT6-H	Col_rec 221 I [I 220 Col_rec]

表2. TPPT6/8/12和TPPT6-H的相转变温度和焓变

Table 2. Phase transition temperature and enthalpy change of TPPT6/8/12 and TPPT6-H

图6. TPPT6/8/12和TPPT6-H在不同温度下的偏光显微织构照片

Figure 6. POM photo micrographs of TPPT6/8/12 and TPPT6-H

图7. TPPTn液晶相态X-射线粉末散射图. 左图是化合物单一温度X-射线散射图; 右图是不同温度小角/广角X-射线散射合图

Figure 7. Representative SAXS/WAXS patterns of TPPTn compounds at one temperature (left column) and with different temperatures (right column)

图8. TPPTn矩形柱状液晶相(Colrec)可能的二维超分子堆积模型, 一矩形超晶格含两个分子. (a)三聚体分子呈平行排列; (b)三聚体分子呈反平行排列

Figure 8. Two-dimensional supramolecular packing model of TPPTn rectangular columnar liquid crystal phase (Colrec), a rectangular superlattice containing two molecules. (a) parallel and (b) antiparallel arrangements of the trimers

TPPT6	TPPT8	TPPT12
Col_rec a=7.104 nm, b=3.321 nm A=23.5924 nm² V_mol=4.645 nm³ h_mol=0.394 nm, N_mol=2	Col_rec a=8.692 nm, b=3.478 nm A=30.2308 nm² V_mol=5.450 nm³ h_mol=0.360 nm, N_mol=2	Col_rec a=9.868 nm, b=3.885 nm A=38.3372 nm² V_mol=7.255 nm³ h_mol=0.378 nm, N_mol=2

表3. 苯并菲-三嗪星型化合物TPPTn中间相参数

Table 3. Mesophase’s parameters of the star-shaped triphenylene-triazine TPPTn

图9. TPPT6安全墨水示意图. ink 1为TPPT6溶于CHCl3得到的稀溶液; ink 2为ink 1中加入TFA得到的溶液

Figure 9. TPPT6 application as safety ink. ink 1: diluted solution of TPPT6 in CHCl3; ink 2: ink 1 and CF3COOH

图10. TPPT6的电致发光光谱(a), CIE1931色度图(b), 恒定电压下正向电流与光效, 光强关系图(c), 未通电和通电状态下的OLED器件照片(d)

Figure 10. Electroluminescence spectra of TPPT6 (a), CIE 1931 chromaticity diagram (b), forward current versus luminous efficiency at constant voltage, light intensity relationship diagram (c), photos of OLED devices with and without electricity (d)

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