CN114685530B - 一类基于异喹啉的聚集诱导发光分子及其制备方法 - Google Patents
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- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims abstract description 16
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- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical group [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
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- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 2
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
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- 125000005843 halogen group Chemical group 0.000 description 1
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Abstract
本发明公开一类基于异喹啉的聚集诱导发光分子及其制备方法。该荧光探针结构如式I所示，其以邻炔基芳香醛为原料，与2‑氨基苯甲醇发生缩合反应得到。本发明得到聚集诱导发光分子合成简单，条件温和，收率高。本发明的聚集诱导发光分子在生物化学与功能分子材料等领域具有实际的应用价值。
Description
技术领域
本发明涉及的是有机功能分子的合成领域，具体涉及基于异喹啉的聚集诱导发光分子及其制备方法。
背景技术
荧光成像的效果在很大程度上取决于荧光材料的性质。传统的荧光材料易发生聚集导致猝灭现象(ACQ)，在高浓度或聚合状态下的荧光强度弱于溶液中的荧光强度。此外，在图像的视觉跟踪过程中，传统荧光材料的抗光漂白能力较差，背景信号较强，导致假阳性结果，不适合长期跟踪和成像。这些缺点阻碍了传统荧光材料在生物医药领域中的应用，亟需一类新的荧光分子来进行替代。
本世纪初，唐本忠小组观察到六苯基硅杂环戊二烯有螺旋桨式的分子构象，它在溶液中没有荧光，当聚集体形成的时候发出蓝色荧光，于是提出了聚集诱导发光(AIE)的概念。由于分子内旋转或分子内振动受限，AIE分子在固态或高浓度的激发光照射下发出强烈的荧光，而在溶液或溶解态下不发光，正好与ACQ分子现象相反。 AIE现象的发现引起了全世界化学、材料等领域科学家的研究兴趣，他们合成了各种不同的AIE分子，比如苯乙烯类、丙烯腈类、杂环戊二烯类、吡喃类、三苯胺类、氟硼类以及分子内氢键型等化合物。AIE因其特殊的光学性能被广泛应用在化学、生物传感器、细胞成像和OLED等方面。
发明内容
针对上述技术问题，本发明提供一类基于异喹啉的聚集诱导发光分子及其制备方法。
本发明的技术方案为：
一类基于异喹啉的聚集诱导发光分子，具有式（I）所示的结构：
（I）
其中，R基团为为氢、卤素原子、烷基或烷氧基。
上述的基于异喹啉的聚集诱导发光分子的制备方法，包括如下步骤：
取化合物1、适量的2-氨基苯甲醇溶于有机溶剂中，加入一定量的催化剂，所述化合物1与2-氨基苯甲醇物质的量之比为1:3-1:1，所述催化剂的用量为化合物1的5%-100%用量，一定温度条件下搅拌2~24小时，固体完全析出，过滤，粗产物用无水乙醇重结晶，得到淡黄色固体化合物I；即式（I）所示的聚集诱导发光分子。
以上各化合物均以反应式中各化合物下面序号加以区分。
进一步地，合成步骤中，化合物1和2-氨基苯甲醇的物质的量之比优选为1:1。
进一步地，合成步骤中，所述的催化剂优选硝酸银、三氟甲磺酸银、三氟醋酸银。
进一步地，合成步骤中，所述的有机溶剂优选无水乙醇。
本发明的有益效果在于：
（1）本发明提供一类新的聚集诱导发光分子，为荧光功能材料的研究提供了候选物质。
（2）本发明提供了一种聚集诱导发光分子的简洁高效合成方法。
附图说明
图1为本发明实施例2制备的聚集诱导发光分子在不同比例四氢呋喃-水溶液中荧光光谱图，自上而下的曲线代表荧光分子分别在1:99、1:9、2:8、3:7、5:5、6:4、7:3、8:2、9:1的四氢呋喃-水溶液中荧光曲线。
其中，图1中，横坐标表示波长（wavelength），纵坐标表示强度（intensity）。
具体实施方式
以下通过具体实施例对本发明做进一步地详细说明，但不应将此理解为本发明上述主题的范围仅限于以下的实施例。凡基于本发明上述内容所实现的技术均属于本发明的范围。
本发明所用仪器与试剂：
核磁共振仪：Bruker AV-II 500 MHz NMR，TMS为内标，CDCl3为溶剂。
所用试剂均为市售化学纯或分析纯。
实施例1
本发明荧光探针的合成
本发明荧光探针的制备途径如下：
在一个干燥的封管反应器中加入0.2 mmol1，再依次加入0.22 mmol 邻氨基苯甲醇和10% 当量 AgNO3，最后加入2 mL EtOH作溶剂，密封，加入小磁石，放入80℃的油浴锅中搅拌回流12h，TLC跟踪反应，待其基本反应完全后将混合物用乙酸乙酯洗出，加适量硅胶粉将其旋干，用热乙醇重结晶，提纯，过滤得到黄色固体产物I。不同取代基R的产物使用Ia、Ib、Ic、Id、Ie等表示。
（R为甲氧基）, 黄色固体, IR (KBr) cm-13416, 2923, 1617, 1510, 1252,1176, 1030, 700, 622.1H NMR (500 MHz, CDCl3)δ7.031-6.980 (m, 16H), 6.940-6.985(m, 4H), 6.846-6.806 (m, 2H), 6.724 (t,J= 7.5 Hz, 1H), 6.671 (d,J= 8.5 Hz,2H), 6.168 (d,J= 8 Hz, 1H), 5.700 (s, 2H), 5.062 (d,J= 15 Hz, 1H), 4.924 (d,J= 15 Hz, 1H), 3.687 (s, 3H).13C NMR (125 MHz, CDCl3)δ144.2, 143.9, 141.2,141.0, 140.8, 140.7, 140.3, 132.5, 131.7, 131.6, 131.5, 130.9, 130.4, 130.0,129.6, 128.6, 128.0,127.7, 126.6, 126.6, 126.4, 125.8, 125.7, 124.8, 124.3,123.6, 122.8, 113.5, 104.5, 84.9, 68.0, 55.3. HRMS: C43H34NO2for [M + H]+,Calculated 596.2590; found 596.2584.
Ib（R为甲基）, 黄色固体. IR (KBr) cm-13427, 2923, 1606, 1491, 1444,1283, 824, 751, 700, 630.1H NMR (500 MHz, CDCl3)δ7.053-6.980 (m, 16H), 6.944-6.898 (m, 6H), 6.848-6.811 (m, 2H), 6.716 (t,J= 7.5 Hz, 1H), 6.164 (d,J= 8.5Hz, 1H), 5.717 (d,J= 6 Hz, 2H), 5.072 (d,J= 14.5 Hz, 1H), 4.935 (d,J= 15 Hz,1H), 2.227 (s, 3H).13C NMR (125 MHz, CDCl3)δ144.1, 143.8, 141.2, 141.1, 140.7,140.6, 140.2, 137.6, 134.1, 132.4, 131.6, 131.4, 131.2, 130.7, 130.3, 128.7,128.5,127.9, 127.6, 126.5, 126.5, 126.3, 125.7, 125.5, 124.7, 124.2, 123.6,122.7, 104.7, 84.8, 67.9, 21.3. HRMS: C43H34NO for [M + H]+, Calculated580.2640; found 580.2635.
Ic（R为氢）, 黄色固体. Mp. 120-123℃. IR (KBr) cm-13436, 2924, 1599,1491, 1444, 1283, 1029, 762, 700, 635.1H NMR (400 MHz, CDCl3)δ7.123-7.092 (m,16H), 7.044-6.995 (m, 6H), 6.936-6.917 (m, 3H), 6.794 (t,J= 7.6 Hz, 1H),6.233 (d,J= 8 Hz, 1H), 5.828 (d,J= 7.6 Hz, 2H), 5.183 (d,J= 14.8 Hz, 1H),5.044 (d,J= 14.8 Hz, 1H).13C NMR (100 MHz, CDCl3)δ144.0, 143.8, 141.4, 141.1,140.7, 140.5, 140.1, 137.1, 132.5, 131.7, 131.4, 130.6, 130.4, 128.7, 128.6,128.0, 127.9, 127.8, 127.7, 126.5, 126.5, 126.3, 125.7, 125.5,124.7, 124.2,123.7, 122.9, 104.9, 84.8, 68.0. HRMS: C42H32NO for [M + H]+, Calculated566.2484; found 566.2478.
Id（R为氟）, 黄色固体. IR (KBr) cm-13422, 2974, 2924, 1623, 1507, 1491,1283, 1226, 1076, 1048, 880, 750, 700.1H NMR (500 MHz, CDCl3)δ7.039-6.982 (m,16H), 6.942-6.909 (m, 4H), 6.868-6.807 (m, 4H), 6.732 (t,J= 8 Hz, 1H), 6.121(d,J= 8.5 Hz, 1H), 5.698 (s, 2H), 5.082 (d,J= 15 Hz, 1H), 4.940 (d,J= 15 Hz,1H).13C NMR (125 MHz, CDCl3)δ144.1, 143.9, 143.8, 141.6, 140.9, 140.6, 140.2,140.0, 133.2, 132.6, 131.7, 131.5, 131.0, 130.5, 130.5, 129.0, 128.8, 128.0,127.8,127.7, 126.6, 126.6, 126.4, 125.7, 124.9, 124.3, 123.7, 123.2, 115.2(d,J= 21.5 Hz), 105.0, 84.9, 68.1.HRMS: C42H31FNO for [M + H]+, Calculated584.2390; found 584.2384.
Ie（R为氯）, 黄色固体. IR (KBr) cm-13423, 2923, 1618, 1491, 1443, 1407,1283, 1090, 836, 750, 700.1H NMR (400 MHz, CDCl3)δ7.116-7.087 (m, 16H), 7.042-7.006 (m, 6H), 6.969-6.913 (m, 2H), 6.844 (t,J= 7.6 Hz, 1H), 6.226 (d,J= 8.4Hz, 1H), 5.813 (d,J= 8 Hz, 2H), 5.172 (d,J= 14.8 Hz, 1H), 5.032 (d,J= 14.8Hz, 1H).13C NMR (100 MHz, CDCl3)δ144.0, 143.8, 143.7, 141.7, 140.9, 140.5,139.8, 135.6, 133.7, 132.5, 131.6, 131.4, 130.4,130.3, 129.9, 128.6, 128.3,127.9, 127.7, 127.7, 126.6, 126.5, 126.4, 125.8, 124.9, 124.1, 123.8, 123.1,105.4, 84.7, 68.0. HRMS: C42H31ClNO for [M + H]+, Calculated 600.2094; found600.2089.
实施例2
荧光分子Ie在不同比例四氢呋喃-水溶液中荧光光谱图
取Ie的标准四氢呋喃溶液，与水配制成含四氢呋喃比例为1:99、1:9、2:8、3:7、5:5、6:4、7:3、8:2、9:1的四氢呋喃-水溶液，保持Ie的浓度始终为10微摩尔每升，荧光光谱仪分别记录500 nm处荧光强度的变化。以荧光强度为纵坐标，发射波长为横坐标作图，荧光强度变化曲线如图1所示。
Claims (4)
1.一类基于异喹啉的聚集诱导发光分子，其特征在于，具有式(I)所示的结构：
其中，R基团为H、Cl、F、OMe、Me。
2.权利要求1所述的基于异喹啉的聚集诱导发光分子的制备方法，其特征在于，包括如下步骤：
取化合物1、适量的2-氨基苯甲醇溶于有机溶剂中，加入一定量的催化剂,所述催化剂选自硝酸银、三氟甲磺酸银或三氟醋酸银，所述化合物1与2-氨基苯甲醇物质的量之比为1:3-1:1，所述催化剂的用量为化合物1的5％-100％用量，一定温度条件下搅拌2～24小时，固体完全析出，过滤，粗产物用无水乙醇重结晶，得到淡黄色固体化合物I；即式(I)所示的聚集诱导发光分子。
3.根据权利要求2所述的基于异喹啉的聚集诱导发光分子的制备方法，其特征在于合成步骤中，化合物1和2-氨基苯甲醇的物质的量之比为1:1。
4.根据权利要求2所述的异喹啉的聚集诱导发光分子的制备方法，其特征在于，合成步骤中，所述的有机溶剂为甲醇或乙醇。
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| CN113278000A (zh) * | 2021-05-28 | 2021-08-20 | 大连大学 | 一种基于香豆素的红光聚集诱导发光材料及其制备方法 |
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