CN105949227A - 一类新型卤代bodipy荧光化合物及其制备方法 - Google Patents
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Abstract
本发明涉及一类新型卤代BODIPY荧光化合物及其制备方法。采用7，12‑二卤代‑2‑醛基三聚茚和2，6‑二碘代BODIPY在对甲苯磺酸和哌啶催化作用下发生Knoevenagel缩合反应合成。该制备方法具有反应步骤简单、反应条件温和、经济环保、产率高，具有普遍适应性。对BODIPY体系进行溴化或碘化可得到三重态光敏剂，促进系间窜跃效率，提高单线态氧产生能力，进而用于光动力治疗和光催化反应体系中。
Description
技术领域
本发明属于有机化合物合成技术领域，具体涉及一类新型卤代BODIPY荧光化合物及其制备方法。
背景技术
氟硼络合二吡咯(简称BODIPY)衍生物是一类良好的光敏染料，它是由二吡咯亚甲基与三氟化硼形成的复合物。该染料分子具有较高的光热稳定性，可以避免染料自身在荧光分析过程中受激发光的照射、温度的升高或检测环境的改变而导致染料结构迅速降解，保证了光谱分析信号的稳定性。此外，BODIPY类荧光染料具有摩尔吸光系数较高、荧光量子产率高、荧光信号对溶剂极性和pH不敏感、荧光光谱峰窄、荧光寿命长、适中的氧化还原电势、可忽略的三重态等优点；而且BODIPY荧光分子母核相对稳定且具有一定化学活性，结构易于修饰，吸收和发射波长可调变至近红外区。基于以上优点，BODIPY类荧光染料越来越受到人们的关注。
光动力疗法PDT是利用光动力效应进行疾病诊断和治疗的一种新技术，对某些癌症的治疗效果不亚于手术、化疗或放疗，其具有以下几个方面的优点：1)治疗时间短；2)可与手术、放疗和化疗同时应用；3)主要破坏癌细胞，不损伤正常细胞；4)可作多疗程，不会产生耐药性。其基本原理是通过向患者体内注射对肿瘤细胞等生物活性组织有亲和作用的光敏剂，利用肿瘤细胞对光敏剂的选择性摄入和潴留作用，在一定时间内，光敏剂会选择性地富集于病灶区，然后以特定波长的激光照射病灶区，光敏剂吸收光能后由基态跃迁至激发态，而激发态的光敏剂又把能量传递给周围的氧，产生活性很强的单线态氧或超氧阴离子自由基、羟基、过氧化氢等其它活性氧物质(reactive oxygen species，ROS)，进而与相邻的生物大分子发生氧化反应，产生细胞毒性作用，破坏脂质、蛋白、核酸等生物分子的活性，引起细胞器的严重损伤和功能障碍，从而导致肿瘤细胞的死亡，达到治疗目的。
已有文献报道证实，带有重原子(例如：溴原子、碘原子)的BODIPY染料分子在细胞内受光激发时更有利于单线态氧的产生，这对于光动力疾病治疗领域的研究具有重要的意义。相比而言，BODIPY荧光染料被认为是具有较高光稳定性的优良染料，通过将溴、碘原子引入BODIPY的共轭中心，达到引入重原子效应的目的，这类化合物相对于过渡金属配合物来说，分子结构易于修饰并可实现吸收波长从绿光向近红外光的灵活调控且更经济环保。所合成的BODIPY类荧光化合物具有作为光敏剂应用于PDT的应用前景。
发明内容
发明目的：针对现有技术中存在的不足，本发明的目的是提供一类新型卤代BODIPY荧光化合物。本发明的另一目的是提供一种上述新型卤代BODIPY荧光化合物的制备方法。
技术方案：为了实现上述发明目的，本发明采用的技术方案为：
本发明的新型卤代BODIPY荧光化合物，其结构式如下：
式中，R为Br或I。
一种制备上述一类新型卤代BODIPY荧光化合物及其制备方法，步骤如下：
1)在配备有Dean-Stark装置的圆底烧瓶中加入2，6-二碘代BODIPY、7，12-二卤代2-醛基三聚茚和对甲苯磺酸，然后溶于25mL甲苯和2mL哌啶，混合物加热到140℃回流，TLC检测原料反应完全。其中，卤代三聚茚甲醛、对甲苯磺酸和BODIPY衍生物的摩尔比为1∶1∶1。
2)将反应物冷至室温，减压除去有机溶剂，残留物经硅胶柱层析，得到目标产物，暗红色固体。
具体化学反应式如下：
上述步骤(1)中，卤代三聚茚甲醛、对甲苯磺酸与碘代BODIPY的摩尔比为1∶1∶1。
上述步骤(1)中，加入的甲苯和哌啶的用量分别是25mL和2mL。
上述步骤(1)中，催化剂为对甲苯磺酸和哌啶。
上述步骤(2)中，柱层析分离洗脱剂为石油醚∶二氯甲烷＝7∶3～1∶1。
本发明的有益效果
与现有技术相比，本发明的一种新型卤代BODIPY荧光化合物及其制备方法具有的优点有：(1)利用卤代三聚茚基团对碘代BODIPY染料的3-位进行结构修饰，使得该荧光染料的吸收和发射波长红移至600nm以上；(2)摩尔消光系数高、荧光发射光谱窄及溶解性好；(3)该制备方法具有操作简便经济、反应选择性好、得率较高、污染少等优点，使其很容易在细胞成像、光动力疗法等领域推广应用。
附图说明
图1是化合物A的紫外-可见吸收光谱图；
图2是化合物A的荧光发射光谱图；
图3是化合物B的紫外-可见吸收光谱图；
图4是化合物B的荧光发射光谱图。
具体实施方式
下面结合具体附图对本发明做进一步的说明。
用1H-NMR、UV-Vis谱及ESI MASS表征并证实近红外BODIPY类荧光染料的结构。检测所用仪器为：Bruker ARX600型核磁共振仪(TMS为内标，氘代氯仿为溶剂)，岛津UV-3100型紫外-可见分光光度计(扫描范围300～900nm，光路狭缝2nm)，美国Thermo ELECTRONCORPORATION质谱工作站，荧光光谱用美国Amico Bowman Series 2LuminescenceSpectrometer测试。
实施例1
圆底烧瓶中配备有分水器，将2，6-二碘代BODIPY(123.6mg，0.20mmol)，7，12-二溴-2-醛基三聚茚(0.138g，0.2mmol)和对甲苯磺酸(40mg)溶于25mL甲苯和2mL哌啶，混合物加热到140℃回流，收集溶剂直到蒸干。将反应物浓缩，硅胶柱层析，洗脱剂为(石油醚∶CH2Cl2＝1∶1)，得到暗红色固体A(36.0mg，13.88％)。Esi-MS：calcd for C62H81BBr2F2I2N21296.58589，found：1296.15051(M+)；1H NMR：(600MHz，CDCl3)δ8.36(d，J＝8.40Hz，1H)，8.26(d，J＝16.80Hz，1H)，8.22(d，J＝8.40Hz，1H)，8.17(d，J＝8.40Hz，1H)，7.79(t，J＝16.80Hz，2H)，7.60-7.58(m，3H)，7.54-7.51(m，2H)，7.00(s，2H)，3.03-2.91(m，6H)，2.74(s，3H)，2.38(s，3H)，2.23-2.09(m，12H)，1.50(s，3H)，1.43(s，3H)，0.24-0.21(m，18H)；UV-vis：315nm，336nm，366nm，605nm(图1)；Emission Wavelength：629nm(图2)。
实施例2
圆底烧瓶中配备有分水器，将2，6-二碘代BODIPY(185.4mg，0.30mmol)，7，12-二碘-2-醛基三聚茚(237.7mg，0.30mmol)和对甲苯磺酸(50mg)溶于25mL甲苯和2mL哌啶，混合物加热到140℃回流，收集溶剂直到蒸干。将反应物浓缩，硅胶柱层析，洗脱剂为(石油醚∶CH2Cl2＝7∶3)，得到暗红色固体B(62.0mg，14.86％)。Esi-MS：calcd for C62H61BF2I4N2：1390.10751，found：1390.10938(M+)；1H NMR：(600MHz，CDCl3)δ8.35(d，J＝8.40Hz，1H)，8.26(d，J＝16.20Hz，1H)，8.10(d，J＝8.40Hz，1H)，8.05(d，J＝8.40Hz，1H)，7.79-7.71(m，6H)，7.57(s，1H)，7.00(s，2H)，3.01-2.89(m，6H)，2.73(s，3H)，2.38(s，3H)，2.23-2.08(m，12H)，1.50(s，3H)，1.43(s，3H)，0.24-0.20(m，18H)；UV-vis：318nm，605nm(图3)；Emission Wavelength：628nm(图4)。
Claims (7)
1.一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于，其结构通式如下：
式中，R为Br或I。
2.权利要求1所述一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于：以7，12-二卤代-2-醛基三聚茚和2，6-二碘代BODIPY为原料，在对甲苯磺酸和哌啶的催化作用下生成目标物，步骤如下：
1)在无水条件下，在配备有Dean-Stark装置的圆底烧瓶中加入碘代BODIPY、卤代三聚茚甲醛和对甲苯磺酸，然后溶于25mL甲苯和2mL哌啶，混合物加热到140℃回流，TLC检测反应原料点消失，除去有机溶剂。其中，卤代三聚茚甲醛、对甲苯磺酸和碘代BODIPY衍生物的摩尔比为1∶1∶1。
2)将反应物冷至室温，减压蒸干溶剂，硅胶柱层析，得到暗红色固体产物。
3.根据权利要求2所述的一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于，步骤1)中，需要配备有Dean-Stark装置。
4.根据权利要求2所述的一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于，步骤1)中，7，12-二卤代2-醛基三聚茚、对甲苯磺酸和2，6-二碘代BODIPY衍生物的摩尔比为1∶1∶1。
5.根据权利要求2所述的一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于，步骤1)中，催化剂为重结晶过的对甲苯磺酸。
6.根据权利要求2所述的一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于，步骤1)中，甲苯和哌啶的用量分别是25mL和2mL。
7.根据权利要求2所述的一类新型卤代BODIPY荧光化合物及其制备方法，其特征在于，步骤2)中，柱层析分离洗脱剂为石油醚∶二氯甲烷＝7∶3～1∶1。
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| CN106905355A (zh) * | 2017-02-28 | 2017-06-30 | 南京林业大学 | 一类近红外碘代氟硼二吡咯光敏剂及其制备方法 |
| CN108976252A (zh) * | 2017-12-14 | 2018-12-11 | 南京林业大学 | 一种三聚茚基bodipy－香豆素星型化合物的制备方法 |
| CN109456348A (zh) * | 2018-12-10 | 2019-03-12 | 南京林业大学 | 一种2,6-二乙炔基三聚茚基bodipy类近红外荧光染料及其制备方法 |
| CN110003461A (zh) * | 2019-04-15 | 2019-07-12 | 苏州大学 | 多碘修饰的氟硼二吡咯类衍生物及其制备方法和应用 |
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| CN106905355A (zh) * | 2017-02-28 | 2017-06-30 | 南京林业大学 | 一类近红外碘代氟硼二吡咯光敏剂及其制备方法 |
| CN108976252A (zh) * | 2017-12-14 | 2018-12-11 | 南京林业大学 | 一种三聚茚基bodipy－香豆素星型化合物的制备方法 |
| CN108976252B (zh) * | 2017-12-14 | 2020-09-15 | 南京林业大学 | 一种三聚茚基bodipy-香豆素星型化合物的制备方法 |
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| CN109456348B (zh) * | 2018-12-10 | 2021-05-04 | 南京林业大学 | 一种2，6-二乙炔基三聚茚基bodipy类近红外荧光染料及其制备方法 |
| CN110003461A (zh) * | 2019-04-15 | 2019-07-12 | 苏州大学 | 多碘修饰的氟硼二吡咯类衍生物及其制备方法和应用 |
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