推拉电子基团区域异构苯并咪唑的发射行为与力致荧光变色性能研究

doi:10.6023/A23070349

摘要/Abstract

以芘基和4-腈基苯基为取代基, 分别合成了两者在苯并咪唑环上N₁位与C₂位区域异构的两个化合物BIM_NPy和BIM_CPy, 研究了两种化合物在溶液中以及固态下的荧光发射性质与力致荧光变色行为. 在溶液中, BIM_CPy的荧光发射波长表现出中等幅度的正向溶剂变色效应, 而BIM_NPy的荧光发射波长则对溶剂极性的变化无响应. 两种化合物的晶体在受力后均出现发射波长的蓝移, 且在BIM_NPy晶体上产生的力致荧光变色活性比在BIM_CPy晶体上更为显著. 此外, BIM_NPy的力致荧光变色性在溶剂熏蒸及热退火状态下均可逆, 并在室温下具有部分自恢复特性; BIM_CPy的力致荧光变色性在溶剂熏蒸下可逆而在热退火处理时不可逆. 根据示差热扫描、粉末与单晶衍射、发射衰变光谱以及理论计算的结果, 对两种化合物发射行为差异性的原因进行了分析与探讨, 认为溶液态下的差异起源于高能级电子激发态的发射特征不同而固态下的差异起源于分子堆积模式的区别, 但推拉电子基团区域异构所引起的分子偶极矩以及π-共轭程度的变化则是异构体产生宏观性能不同的根本原因.

关键词: 力致荧光变色, 区域异构, 苯并咪唑, 芘基, 分子堆积

Through the oxidation-cyclization of N-(4-cyanophenyl)-o-phenylenediamine and 1-pyrenylaldehyde or N-(1- pyrenyl)-o-phenylenediamine and 4-cyanobenzaldehyde in dimethyl sulfoxide under air, the two isomers BIM_NPy and BIM_CPywith pyrenyl and 4-cyanophenyl interchanged at N₁ and C₂ position on benzo[d]imidazole core were prepared while the photophysical properties of the double isomers in both solution and solid state were investigated. In solution, the emission of BIM_CPy exhibited a moderate solvatochromic effect but the emission of BIM_NPy was inert to the change of solvent polarity. The crystals of the two isomers displayed the blue-shifted mechanofluorochromic (MFC) behavior in response to force stimuli, but BIM_NPy crystals possess the larger MFC activity. Moreover, the MFC on BIM_NPy was reversible by fuming in solvent vapor or annealing and could be partly self-recovered at room temperature thanks to the less dense intermolecular interactions. However, the MFC on BIM_CPy was irreversible under annealing and could only be recovered by fuming due to the indispensability of solvent molecules to form crystal lattices. In aid of differential scanning calorimetry, powder and single crystal X-ray diffraction, emission decay spectra as well as theoretical calculations, the reasons for the different emission behavior of the two isomers in solution and solid state were explored. It was revealed that the S₂ excited state with both intramolecular charge transfer (ICT) and local emission (LE) features may account for the sensitive solvatochromism of BIM_CPy, while the S₂ excited state with only LE emission feature may be responsible for the inert solvatochromism of BIM_NPy. Moreover, the different solid-state emission performance and MFC activity should be attributed to the particular molecular packing in crystals of the two isomers. Fundamentally, the varied dipole moments and the distinguishing π-conjugation extents induced by the region-isomerization of pyrenyl and 4-cyanophenyl with the push-pull electronic capability could be considered as the primary cause for the remarkably macroscopic differences of physical properties on the two isomers.

Key words: mechanofluorochromism, region-isomerization, benzo[d]imidazole, pyrenyl, molecular packing

引用此文

贾彦荣, 徐凯, 赵彦英, 倪华钢, 吴滢, 夏敏. 推拉电子基团区域异构苯并咪唑的发射行为与力致荧光变色性能研究[J]. 化学学报, 2023, 81(12): 1716-1723.

Yanrong Jia, Kai Xu, Yanying Zhao, Huagang Ni, Ying Wu, Min Xia. Research on Emission Behavior and Mechanofluorochromic Activity of Benzo[d]imidazoles with Region-isomerized Push-Pull Groups[J]. Acta Chimica Sinica, 2023, 81(12): 1716-1723.

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图/表 10

图1. 具有区域异构或位置异构的MFC活性体系的代表性结构(FS: 力刺激作用)

Figure 1. Representative structures of MFC-active systems with region- or position-isomerized groups (FS: force stimuli)

图2. BIMNPy和BIMCPy的合成路线

Figure 2. Synthetic routes of BIMNPy and BIMCPy

图3. BIMNPy (a)和BIMCPy (b)在不同极性溶剂中的吸收光谱(左侧虚线)与发射光谱(激发波长: 340 nm, 右侧实线) (插图: 365 nm紫外光照下溶液的荧光照片. 1: 正己烷; 2: 苯; 3: 乙酸乙酯; 4: 二氯甲烷; 5: 乙腈)

Figure 3. Absorption (dash lines on left) and emission spectra (λex=340 nm, solid lines on right) of BIMNPy (a) and BIMCPy (b) in different solvents (inserted: photos of solution under 365 nm UV light. 1: n-hexane; 2: benzene; 3: ethyl acetate; 4: dichloromethane; 5: acetonitrile)

图4. BIMNPy (a)和BIMCPy (b)在气态和乙腈溶液中的前线轨道能量和发射跃迁特性(f : 跃迁振子强度; ΔE: 轨道能级的能量差)

Figure 4. Orbit energy levels and emission transition characteristics of BIMNPy (a) and BIMCPy (b) in gas phase and in acetonitrile solution (f: transition oscillator strength; ΔE: energy gap between orbits)

图5. 自由态(绿色)和结晶态(橙色)中BIMNPy和BIMCPy的分子二面角以及晶相中分子的偶极矩

Figure 5. Dihedral angles of BIMNPy and BIMCPy in free (green) and crystalline state (orange), and molecular dipole moments in crystalline state

图6. (a), (b) BIMNPy晶体中和(c)~(e) BIMCPy晶体中的分子堆积及分子间相互作用

Figure 6. Molecular packings and intermolecular interactions in (a), (b) BIMNPy crystal and (c)~(e) BIMCPy crystal

图7. BIMNPy (a)和BIMCPy (b)在不同条件下的固态发射光谱和365 nm紫外光照射下的荧光照片

Figure 7. Solid-state emission spectra and photos by 365 nm UV light of BIMNPy (a) and BIMCPy (b) under different conditions

图8. BIMNPy (a)和BIMCPy (b)在不同条件下的固态发射衰变光谱图

Figure 8. Emission decay spectra of BIMNPy (a) and BIMCPy (b) under different conditions

图9. BIMNPy (a)和BIMCP y (b)在不同条件下的PXRD图

Figure 9. PXRD patterns of BIMNPy (a) and BIMCPy (b) under different conditions

图10. BIMNPy (a)和BIMCPy (b)在不同固体状态下的DSC曲线

Figure 10. DSC of BIMNPy (a) and BIMCPy (b) under different solid- state conditions

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