CN110343126A - 吡啶/吡啶季铵盐取代bodipy类化合物及其应用 - Google Patents

吡啶/吡啶季铵盐取代bodipy类化合物及其应用 Download PDF

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CN110343126A
CN110343126A CN201910655371.6A CN201910655371A CN110343126A CN 110343126 A CN110343126 A CN 110343126A CN 201910655371 A CN201910655371 A CN 201910655371A CN 110343126 A CN110343126 A CN 110343126A
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quaternary ammonium
ammonium salt
pyridine
bdp
pyridin
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赵伟利
张健
王先辉
金月
陶远芳
刘唱
陈淼
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Shanghai Annengjian Biopharmaceutical Technology Co ltd
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Abstract

本申请公开一类吡啶或吡啶季铵盐取代BODIPY类化合物，所述化合物具有下述通式(I)、(II)或（III）的结构：其中：Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶‑2‑基或其季铵盐、吡啶‑3‑基或其季铵盐、吡啶‑4‑基或其季铵盐，且Ar1、Ar2和Ar3至少一个为下述中的一种：吡啶‑2‑基或其季铵盐、吡啶‑3‑基或其季铵盐、吡啶‑4‑基或其季铵盐；所述季铵盐为甲基吡啶季铵盐、乙基吡啶季铵盐或苄基吡啶季铵盐，其阴离子为溴负离子、碘负离子或三氟甲磺酸负离子；R1、R2独立地选自H、C1‑C3烷基、C1‑C3烷氧基、F、Cl、Br或OH。

Description

吡啶/吡啶季铵盐取代BODIPY类化合物及其应用
技术领域
本发明属于光功能材料领域，尤其涉及一类吡啶/吡啶季铵盐取代BODIPY类化合物及其应用。
背景技术
随着生物科学与技术的不断发展，人类对生命活动本质的研究与探索越来越多的关注到亚细胞层面活性物质的作用机制，其中对细胞器及其内部活性物质的可视化追踪是研究机制的重要手段。线粒体是细胞中非常重要的一个动态细胞器，是细胞的“动力工厂”，在细胞的生命活动中扮演着多种重要的角色，如在调节细胞氧化还原电位和信号转导、调节细胞分化与凋亡、基因表达、跨膜转运等方面发挥着重要作用。大量研究表明，线粒体的数量、分布、结构与功能变化等与神经退行性病变(如阿尔兹海默症、帕金森症)、代谢型疾病(如肥胖症、II型糖尿病)、心血管疾病及癌症等病症关系密切。因此，可视化追踪线粒体自身变化及其内部活性物质对深入揭示生物体生命活动规律有十分重要的生物学意义。
作为一种灵敏的非侵入性检测技术，荧光探针已广泛应用于生物检测和机制研究。在近红外(650-900nm)光区，组织的吸收、散射和自发荧光背景都远远低于可见光区，因此近红外荧光探针在抗背景干扰、生物安全性、检测灵敏度等方面有显著优势，特别适合于生物活体内的无损监测。
荧光探针的关键组成部分就是荧光染料，需要具备生物相容性好、荧光量子产率高、光稳定性好、对环境不敏感等优点。氟硼二吡咯甲川类染料(BODIPY)具有合成简单、可修饰位点多、荧光量子产率高、光稳定性好、对pH和极性不敏感等优点；另外更重要的是，BODIPY类荧光染料的分子量相对较小、生物相容性好、容易渗透入活细胞、非常适用于生物荧光成像，尤其适合长时间荧光追踪。长波长的BODIPY染料因较低的背景荧光更适合于分子影像研究，但长波长的BODIPY染料因含有多个芳环而具有强疏水性。
发明内容
本发明的目的在于提供一类吡啶/吡啶季铵盐取代BODIPY类化合物及其应用。
本发明通过分子设计，把吡啶/吡啶季铵盐修饰到BODIPY母核上，得到通式(I)、(II)或(III)的长波长BODIPY类化合物：
其中：
Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐，且Ar1、Ar2或Ar3至少一个为下述中的一种：吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐；所述季铵盐为甲基吡啶季铵盐、乙基吡啶季铵盐或苄基吡啶季铵盐，其阴离子为溴负离子、碘负离子或三氟甲磺酸负离子；
R1、R2独立地选自H、C1-C3烷基、C1-C3烷氧基、F、Cl、Br或OH；
所述Ar1、Ar2、Ar3中为带有取代基的吡啶环或其季铵盐时，取代基任选自以下基团：F、Cl、Br、羟基、氨基、硝基、氰基、三氟甲基、三氟甲氧基、C1-C3烷基或C1-C3烷氧基。
与苯基取代的类似物相比含吡啶的BODIPY染料保持良好的荧光量子产率，轻微的波长红移，和较大的Storks位移；并环结构将更有利于长波长吸收和发射。将吡啶季铵盐化进一步导致波长红移及Storks位移增大，有利于分子影像方面的应用。更为重要的是，吡啶季铵盐可能改善BODIPY染料的水溶性，且赋予其对细胞线粒体的靶向性。
本发明的优选化合物为Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐，且Ar1、Ar2或Ar3至少一个为下述中的一种：吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐；所述季铵盐为甲基吡啶季铵盐、乙基吡啶上述结构通式(I)、(II)或(III)中季铵盐，其阴离子为溴负离子或碘负离子；R1、R2独立地选自H、甲基、甲氧基、F、Cl、Br或OH；所述Ar1、Ar2、Ar3中可带有F、Cl、Br、甲基或甲氧基。
更为优选的化合物为：上述结构通式(I)、(II)或(III)中Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐，且Ar1、Ar2或Ar3至少一个为下述中的一种：吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐。所述季铵盐为甲基吡啶季铵盐，其阴离子为碘负离子；R1、R2独立地选自H、甲基或甲氧基；所述Ar1、Ar2、Ar3中可带有取代基，任选自以下基团：F、Cl、Br、羟基或甲氧基。
最为优选的化合物则选自下述化合物结构：
以化合物BDP-1和BDP-14为例，本发明的化合物制备如下：
本发明另一方面目的是提供所述的一类吡啶/吡啶季铵盐取代BODIPY化合物在生物成像，荧光探针，荧光传感器，光电材料等不同领域的应用，尤其是在制备细胞荧光成像剂中的应用。
本发明的化合物提供一种3-位或5-位吡啶/吡啶季铵盐取代BODIPY染料，该荧光染料紫外可见吸收光谱和荧光发射光谱半峰宽窄，摩尔消光系数高，荧光量子产率高，且光稳定好，能够用于细胞成像，线粒体靶向成像，荧光探针，荧光传感器，光电材料等不同领域。
本发明的化合物进行了细胞成像和线粒体靶向成像，现实出很好的成像效果，其中BDP-1能够用于HeLa细胞的成像，BDP-14能够用于HeLa细胞内线粒体的靶向成像。
本发明中，所采用的HeLa细胞是本领域技术人员可通过市购的途径所获得的。
附图说明
图1是化合物BDP-1的HeLa细胞成像实验结果图：(A)对照组荧光图像；(B)对照组明场与暗场图片重合图；(C)暗场中化合物BDP-1的红色荧光图像；(D)明场与暗场化合物BDP-1的红色荧光重合图；比例尺：50μm；
图2是化合物BDP-14的线粒体定位实验结果图；(A)明场中细胞形态；(B)Mito-Tracker Green(200nM)的绿色荧光图像；(C)化合物BDP-14的红色荧光图像；(D)图A，B和C的叠合图；比例尺：50μm。
具体实施方式
通过下面的实施例可以对本发明进行详细的描述，但并不意味着对本发明任何不利限制。所描述的实施例是本发明的一部分实施例，而不是全部实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前体下所获得的所有实施例，都属于本发明保护范围。
对于以下全部实施例，可使用本领域技术人员已知的标准操作和纯化方法。除非另有说明，所有温度以℃(摄氏度)表示。化合物的结构式通过1H NMR和13C NMR来确定。
实施例1：合成化合物BDP-1
在冰水浴中，将三氯氧磷(0.23g，1.5mmol)缓慢滴加到DMF(0.11g，1.5mmol)中，在冰浴中搅拌10min后，撤去冰浴，在室温下搅拌15min，然后缓慢滴加溶于1,2-二氯乙烷(20mL)的2-(4’-甲氧基苯)-4-(2’-吡啶)吡咯(0.15g，0.60mmol)溶液，通过Vilsmeier反应，反应结束，用乙酸乙酯和饱和NaCl水溶液萃取后，分离有机相，用无水Na2SO4干燥并浓缩，通过硅胶柱层析(乙酸乙酯/石油醚＝2:1，v/v)纯化粗产物，得到白色的粉末状固体2-(4’-甲氧基苯)-4-(2’-吡啶)-5-甲酰基吡咯；氮气保护下，将所得2-(4’-甲氧基苯)-4-(2’-吡啶)-5-甲酰基吡咯(0.13g，0.45mmol)与2-(4’-甲氧基苯)-4-苯基吡咯(0.12g，0.45mmol)溶于重蒸干燥的1,2-二氯乙烷(50mL)中，缓慢滴加三氯氧磷(76mg，0.54mmol)，室温搅拌12h后，体系由无色变为褐绿色，加入三乙胺(0.34g，3.4mmol)，室温搅拌10min后，缓慢滴加三氟化硼乙醚(0.54g，3.8mmol)，此时，有大量白烟冒出；室温搅拌4h后，体系由褐绿色变为红色，将有机溶剂减压旋干后，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到具有绿色金属光泽固体BDP-1(28mg，11％)。1H NMR(400MHz,CDCl3)δ8.692(s,1H),8.606(d,J＝4.7Hz,1H),7.988(d,J＝8.8Hz,2H),7.928(d,J＝8.8Hz,2H),7.696(t,J＝7.6Hz,1H),7.630(d,J＝7.0Hz,3H),7.516(t,J＝7.3Hz,2H),7.454(t,J＝7.3Hz,1H),7.180(t,J＝5Hz,1H),6.980(d,J＝8.7Hz,4H),6.905(s,1H),6.768(s,1H),3.854(s,6H)；13C NMR(150MHz,CDCl3)δ161.078,160.66,158.32,155.72,152.86,149.73,146.29,140.03,136.68,135.39,134.49,133.50,131.36,131.32,131.28,131.06,131.02,130.98,129.61,129.04,128.97,128.77,125.26,124.86,122.51,118.99,117.78,113.93,113.82,55.33,55.31,29.74。
实施例2：合成化合物BDP-2
化合物BDP-2的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(4’-甲氧基苯)-4-(3’-吡啶)吡咯(0.15g，0.60mmol)，2-(4’-甲氧基苯)-4-(2’-噻吩)吡咯(0.11g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有绿色金属光泽固体BDP-2(45mg，18％)。1HNMR(400MHz,DMSO)δ8.946(s,1H),8.680(d,J＝6.1Hz,1H),8.152(d,J＝7.9Hz,1H),7.945(dd,J＝9.0,2.3Hz,4H),7.786(d,J＝5.0Hz,1H),7.685(s,1H),7.654(d,J＝3.4Hz,1H),7.590(t,J＝6.4Hz,1H),7.255(t,J＝4.4Hz,1H),7.187(s,1H),7.095(s,1H),7.071(dd,J＝9.0,2.3Hz,4H),3.842(s,6H)；13C NMR(100MHz,DMSO)δ161.33,161.24,157.74,156.70,150.170,149.47,141.150,138.04,136.53,134.49,133.97,133.81,131.57,131.54,129.53,129.33,129.21,128.95,125.31,124.60,124.38,119.99,118.61,114.46,114.42,56.51,55.86,19.03。
实施例3：合成化合物BDP-3
化合物BDP-3的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(4’-甲氧基苯)-4-(4’-吡啶)吡咯(0.15g，0.60mmol)，7-甲氧基-3-苯基-4,5-二氢-苯并吡咯(0.12g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有绿色金属光泽固体BDP-3(134mg，16％)。1H NMR(400MHz,DMSO)δ8.709(d,J＝5.1Hz,2H),8.543(d,J＝9.5Hz,1H),7.939(d,J＝8.7Hz,2H),7.737(d,J＝5.2Hz,2H),7.653–7.472(m,5H),7.266(s,1H),7.163–6.982(m,5H),3.868(d,J＝3.0Hz,6H),2.933(t,J＝6.2Hz,2H),2.779(t,J＝6.6Hz,2H)；13C NMR(100MHz,DMSO)δ.162.42,160.68,155.09,153.18,149.32,145.26,141.01,137.63,136.74,132.50,131.73,131.21,130.10,129.51,129.33,125.25,123.89,122.76,119.89,118.73,114.78,114.39,113.66,56.05,55.82,30.19,21.04。
实施例4：合成化合物BDP-4
化合物BDP-4的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(4’-甲氧基苯)-4-(2’-吡啶)吡咯(0.15g，0.60mmol)，7-甲氧基-3-(2’-噻吩)-4,5-二氢-苯并吡咯(0.12g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有黄色金属光泽固体BDP-4(66mg，20％)。1H NMR(400MHz,DMSO)δ8.957(s,1H),8.666(d,J＝5.4Hz,1H),8.501(d,J＝8.7Hz,1H),8.012(d,J＝8.0Hz,1H),7.973–7.884(m,4H),7.459–7.417(m,1H),7.400–7.347(m,2H),7.337(s,1H),7.101(d,J＝8.9Hz,2H),7.047–6.988(m,2H),3.867(s,6H),2.953(t,J＝6Hz,2H),2.887(t,J＝6Hz,2H)；13C NMR(100MHz,DMSO)δ162.06,160.66,154.10,153.65,152.79,150.07,144.56,138.12,137.79,135.97,133.67,133.42,132.80,131.21,131.18,130.70,130.68,130.47,129.58,129.02,125.83,125.36,123.39,123.23,120.04,118.04,114.66,114.33,113.44,55.96,55.80,55.37,30.09,21.36。
实施例5：合成化合物BDP-5
化合物BDP-5的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，7-甲氧基-3-(3’-吡啶)-4,5-二氢-苯并吡咯(0.17g，0.60mmol)，2-(4’-甲氧基苯)-4-苯基吡咯(0.11g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有黄色金属光泽固体BDP-5(55mg，21％)。1HNMR(400MHz,CDCl3)δ8.707–8.633(m,3H),7.984(d,J＝8.7Hz,2H),7.676(d,J＝7.8Hz,1H),7.493–7.374(m,6H),7.107(s,1H),7.026(d,J＝8.7Hz,2H),6.939(dd,J＝8.8,2.3Hz,1H),6.811(s,1H),6.683(s,1H),3.894(s,3H),3.867(s,3H),2.899(t,J＝6.7Hz,2H),2.742(t,J＝6.8Hz,2H)；13C NMR(100MHz,CDCl3)δ161.45,160.68,155.85,152.87,150.08,149.29,143.67,143.29,136.77,135.59,135.57,135.56,133.87,133.85,133.72,131.17,131.13,131.09,129.07,128.69,128.44,125.41,123.58,122.73,120.66,118.35,114.34,113.87,112.70,55.37,55.336,30.67,21.05。
实施例6：合成化合物BDP-6
化合物BDP-6的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，7-甲氧基-3-(4’-吡啶)-4,5-二氢-苯并吡咯(0.17g，0.60mmol)，2-(4’-甲氧基苯)-4-(2’-噻吩)吡咯(0.12g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有绿色金属光泽固体BDP-6(42mg，13％)。1H NMR(400MHz,DMSO)δ8.774(d,J＝5.9Hz,2H),8.484(d,J＝8.8Hz,1H),7.960(d,J＝8.9Hz,2H),7.739(dd,J＝3.6,1.2Hz,1H),7.612(d,J＝6.0Hz,2H),7.574(dd,J＝5.1,0.9Hz,1H),7.502(s,1H),7.233(dd,J＝5.2,4Hz,1H),7.102(d,J＝8.9Hz,2H),7.018(d,J＝8.5Hz,3H),3.864(d,J＝3.3Hz,6H),2.926(t,J＝6.8Hz,2H),2.777(t,J＝6.8Hz,2H)；13C NMR(100MHz,DMSO)δ161.88,161.00,155.73,152.51,150.69,144.43,139.84,136.64,136.08,134.89,134.82,133.16,131.50,131.41,131.38,131.34,129.22,129.01,128.41,124.84,124.69,122.26,120.15,117.82,114.74,114.42,113.48,55.96,55.85,30.12,20.89。
实施例7：合成化合物BDP-7
化合物BDP-7的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，7-甲氧基-3-(3’-吡啶)-4,5-二氢-苯并吡咯(0.17g，0.60mmol)，7-甲氧基-3-(2’-噻吩)-4,5-二氢-苯并吡咯(0.12g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有黄色金属光泽固体BDP-7(53mg，15％)。1HNMR(600MHz,CDCl3)δ8.552(d,J＝4.8Hz,2H),8.448(s,1H),8.409(d,J＝4.8Hz,1H),7.481(d,J＝7.8Hz,1H),7.195(d,J＝4.6Hz,2H),7.027(s,2H),6.914(t,J＝4.5Hz,1H),6.845(d,J＝5.1Hz,1H),6.769(d,J＝9.0Hz,2H),6.592(s,2H),3.658(s,6H),2.754–2.474(m,8H)；13C NMR(150MHz,CDCl3)δ160.44,160.27,151.25,150.09,149.48,148.35,142.39,142.15,136.16,134.76,134.10,133.47,133.06,130.69,129.87,129.80,129.72,129.67,129.59,129.52,129.03,128.81,128.44,127.38,127.14,126.48,122.91,120.60,120.48,119.42,113.69,113.63,111.95,111.92,54.72,30.17,30.10,20.71,20.41。
实施例8：合成化合物BDP-8
化合物BDP-8的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-苯基-4-(4’-吡啶)吡咯(0.13g，0.60mmol)，2，4-二(2’-噻吩)-吡咯(0.10g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有绿色金属光泽固体BDP-8(62mg，20％)。1H NMR(600MHz,CDCl3)δ8.491(d,J＝5.1Hz,2H),7.962(d,J＝4.0Hz,1H),7.727(d,J＝7.9Hz,2H),7.423(s,1H),7.307–7.199(m,6H),7.062(d,J＝3.5Hz,1H),7.011(s,1H),6.930(t,J＝6.3Hz 2H),6.698(s,1H),6.567(s,1H)；13C NMR(150MHz,CDCl3)δ161.33,161.24,157.74,156.70,150.17,149.47,141.15,138.04,136.53,134.49,133.97,133.81,131.57,131.54,129.53,129.33,129.21,128.95,125.31,124.60,124.38,119.99,118.61,114.46,114.42,56.51,55.86,19.03。
实施例9：合成化合物BDP-9
化合物BDP-9的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(2’-吡啶)-4-苯基吡咯(0.13g，0.60mmol)，2,4-二苯基吡咯(0.10g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有紫红色金属光泽固体BDP-9(56mg，25％)。1H NMR(400MHz,CDCl3)δ8.708(d,J＝4.6Hz,1H),8.497(d,J＝8.0Hz,1H),7.999(d,J＝7.4Hz,2H),7.805(td,J＝7.9,1.7Hz,1H),7.550(dd,J＝13.9,6.8Hz,6H),7.505–7.396(m,10H),7.317–7.287(m,1H),6.768(s,1H)；13C NMR(100MHz,CDCl3)δ158.93,155.54,150.16,149.39,146.55,145.33,136.58,135.05,134.80,133.47,133.12,132.32,129.99,129.61,129.57,129.53,129.17,129.10,129.02,128.89,128.85,128.75,128.54,128.368,125.17,125.08,124.99,123.83,120.00,119.98,119.58,119.56。
实施例10：合成化合物BDP-10
化合物BDP-10的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(2’-吡啶)-4-苯基吡咯(0.13g，0.60mmol)，2-(4’-甲氧基苯)-4-苯基吡咯(0.11g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有紫红色金属光泽固体BDP-10(66mg，28％)。1H NMR(400MHz,CDCl3)δ9.033(s,1H),8.633(d,J＝3.3Hz,1H),8.378(d,J＝8.0Hz,1H),7.980(d,J＝8.8Hz,2H),7.542–7.450(m,10H),7.440–7.381(m,2H),6.994(d,J＝8.8Hz,2H),6.788(s,1H),6.731(s,1H),3.871(s,3H)；13C NMR(100MHz,CDCl3)δ161.50,159.74,151.78,149.82,149.73,147.29,144.31,136.82,136.76,136.71,135.77,135.75,133.82,133.45,132.98,131.47,131.43,131.39,129.16,129.13,129.11,128.83,128.78,128.67,127.07,124.26,123.16,119.72,119.70,118.02,118.002,117.99,114.05,55.37。
实施例11：合成化合物BDP-11
化合物BDP-11的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(4’-吡啶)-4-苯基吡咯(0.13g，0.60mmol)，7-甲氧基-3-苯基-4,5-二氢-苯并吡咯(0.12g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有墨绿色金属光泽固体BDP-11(80mg，20％)。1H NMR(400MHz,DMSO)δ8.843(d,J＝6.2Hz,2H),8.618(d,J＝8.7Hz,1H),8.208(d,J＝6.2Hz,2H),7.675–7.470(m,9H),7.428(t,J＝7.3Hz,1H),7.269(d,J＝6.8Hz,2H),7.133–7.031(m,2H),3.898(s,3H),2.966(t,J＝6.5Hz,2H),2.804(t,J＝6.6Hz,2H)；13C NMR(100MHz,DMSO)δ163.24,157.74,157.65,146.54,146.39,142.22,140.31,138.46,138.41,133.65,133.42,133.18,131.78,131.28,130.08,129.62,129.53,129.05,128.96,124.34,123.52,119.48,119.33,114.90,114.04,56.18,55.37,30.05,21.02。
实施例12：合成化合物BDP-12
化合物BDP-12的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(3’-吡啶)-4-苯基吡咯(0.13g，0.60mmol)，2-(2’-噻吩)-4-苯基吡咯(0.10g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有绿色金属光泽固体BDP-12(45mg，18％)。1H NMR(400MHz,DMSO)δ9.141(s,1H),8.686(d,J＝4.0Hz,1H),8.385(d,J＝8.0Hz,1H),8.123(d,J＝3.4Hz,1H),7.973(d,J＝4.8Hz,1H),7.708(d,J＝7.0Hz,4H),7.624–7.442(m,8H),7.337(s,1H),7.303(t,J＝4.2Hz 1H),7.174(s,1H)；13C NMR(100MHz,DMSO)δ152.06,151.13,150.54,149.94,146.75,144.28,136.75,135.37,133.90,133.36,133.26,133.22,133.16,133.12,132.46,129.90,129.68,129.53,129.42,129.37,129.26,128.78,126.74,123.89,120.18,119.33。
实施例13：合成化合物BDP-13
化合物BDP-13的合成方法同化合物BDP-1的合成路线，使用三氯氧磷(0.23g，1.5mmol)，DMF(0.11g，1.5mmol)，2-(4’-吡啶)-4-苯基吡咯(0.13g，0.60mmol)，2,4-二(2’-噻吩)-吡咯(0.11g，0.45mmol)，三氯氧磷(76mg，0.54mmol)，三乙胺(0.34g，3.4mmol)，三氟化硼乙醚(0.54g，3.8mmol)，用氧化铝柱层析(二氯甲烷/石油醚＝1:3，v/v)分离得到有墨绿色金属光泽固体BDP-13(45mg，18％)。1H NMR(400MHz,CDCl3)δ8.744(d,J＝6.0Hz,2H),8.207(d,J＝3.6Hz,1H),7.976(d,J＝7.6Hz,2H),7.681(s,1H),7.572–7.424(m,7H),7.315(d,J＝3.2Hz,1H),7.182(t,J＝4.4Hz 2H),6.952(s,1H),6.818(s,1H)；13C NMR(100MHz,DMSO)δ155.57,151.66,150.87,140.60,139.36,134.93,133.72,133.54,133.34,132.84,132.46,130.26,130.20,129.70,129.52,129.46,128.93,125.18,123.66,120.15,118.92,79.65。
实施例14：合成化合物BDP-14
将化合物BDP-1(11.2mg，0.02mmol)溶于2.0mL甲苯中，加入0.30mL碘甲烷，110℃回流4h，减压旋干有机溶剂，用石油醚/二氯甲烷重结晶，得到具有紫色金属光泽固体BDP-14(10mg,99％)。1H NMR(400MHz,DMSO)δ9.193(d,J＝6.2Hz,1H),8.660(t,J＝7.9Hz,1H),8.371(d,J＝7.7Hz,1H),8.159(t,J＝7.4Hz,1H),8.079(d,J＝9.0Hz,2H),7.889(d,J＝8.9Hz,2H),7.737(dd,J＝7.8,1.8Hz,2H),7.562–7.470(m,3H),7.419(s,1H),7.318(d,J＝14.1Hz,2H),7.109(dd,J＝16.2,8.9Hz,4H),4.324(s,3H),3.861(d,J＝10.1Hz,6H)；13CNMR(100MHz,DMSO)δ162.28,161.83,160.95,152.73,148.58,148.29,147.96,145.48,136.50,132.36,132.32,131.39,131.35,130.14,129.83,129.72,129.47,127.39,126.83,124.54,123.65,121.95,120.91,114.74,114.46,56.05,55.87,47.84。
实施例15：合成化合物BDP-15
化合物BDP-15的合成方法同化合物BDP-14合成路线，使用BDP-2(50mg，0.08mmol)，碘甲烷(1.10mL)，得到有紫黑色金属光泽固体BDP-15(48mg，76％)。1H NMR(400MHz,DMSO)δ9.512(s,1H),9.046(d,J＝5.9Hz,1H),8.910(d,J＝8.1Hz,1H),8.293(dd,J＝8.0,6.2Hz,1H),8.004(d,J＝8.9Hz,2H),7.910(d,J＝8.8Hz,2H),7.862–7.799(m,3H),7.316–7.277(m,2H),7.202(s,1H),7.105(d,J＝8.5Hz,4H),4.447(s,3H),3.862(d,J＝3.0Hz,6H)；13C NMR(100MHz,DMSO)δ161.83,161.13,160.00,154.92,145.39,144.85,144.20,139.74,135.15,135.11,134.15,133.25,132.76,131.94,131.90,131.34,131.31,130.09,129.88,129.58,128.36,125.67,124.55,123.84,120.23,119.60,114.57,114.54,55.98,55.90,48.60。
实施例16：合成化合物BDP-16
化合物BDP-16的合成方法同化合物BDP-14合成路线，使用BDP-3(11.6mg，0.02mmol)，碘甲烷(0.30mL)，得到有紫黑色金属光泽固体BDP-16(13mg，89％)。1H NMR(400MHz,DMSO)δ8.988(d,J＝6.7Hz,2H),8.571(d,J＝9.1Hz,1H),8.349(d,J＝6.7Hz,2H),7.897(d,J＝8.8Hz,2H),7.661(d,J＝6.9Hz,2H),7.626–7.511(m,3H),7.320(s,1H),7.257(s,1H),7.146–7.033(m,4H),4.312(s,3H),3.878(d,J＝8.9Hz,6H),2.961(t,J＝6.6Hz,2H),2.812(t,J＝6.7Hz,2H)；13C NMR(100MHz,DMSO)δ163.18,160.61,157.37,151.83,149.08,146.22,145.92,141.98,138.22,133.13,133.12,132.78,132.42,132.40,131.39,131.13,131.10,131.07,130.18,129.59,129.53,126.01,125.16,122.05,119.39,119.11,119.08,119.05,114.90,114.39,114.00,56.19,55.84,47.64,30.10,21.12。
实施例17：合成化合物BDP-17
化合物BDP-17的合成方法同化合物BDP-14合成路线，使用BDP-4(11.8mg，0.02mmol)，碘甲烷(0.30mL)，得到有棕色金属光泽固体BDP-17(14mg，96％)。1H NMR(400MHz,DMSO)δ9.214(d,J＝6.0Hz,1H),8.670(t,J＝7.7Hz,1H),8.569(d,J＝8.8Hz,1H),8.338(d,J＝7.5Hz,1H),8.166(t,J＝6.4Hz,1H),7.944–7.845(m,3H),7.516(d,J＝2.9Hz,1H),7.418(s,1H),7.286(t,J＝4.4Hz,1H),7.229(s,1H),7.124–7.034(m,4H),4.351(s,3H),3.873(d,J＝9.1Hz,6H),2.947(dd,J＝18.1,7.1Hz,4H)；13C NMR(100MHz,DMSO)δ163.20,160.64,157.75,150.85,149.00,147.95,146.00,145.45,137.72,134.95,133.39,132.37,132.01,131.68,131.29,131.23,130.50,130.24,129.18,127.74,127.17,124.97,122.42,119.80,119.28,114.85,114.44,113.98,56.21,55.86,47.87,29.97,21.41。
实施例18：合成化合物BDP-18
化合物BDP-18的合成方法同化合物BDP-14合成路线，使用BDP-5(11.7mg，0.02mmol)，碘甲烷(0.30mL)，得到有黄黑色金属光泽固体BDP-18(11.5mg，96％)。1HNMR(400MHz,DMSO)δ9.448(s,1H),9.084(d,J＝6.0Hz,1H),8.789(d,J＝8.1Hz,1H),8.493(d,J＝8.8Hz,1H),8.278(t,J＝7.2Hz,1H),8.042(d,J＝8.8Hz,2H),7.774(d,J＝7.2Hz,2H),7.526(t,J＝7.3Hz,2H),7.495–7.441(m,1H),7.386(s,1H),7.156–7.096(m,3H),7.035(d,J＝10.9Hz,2H),4.449(s,3H),3.875(d,J＝6.0Hz,6H),2.955(t,J＝6.6Hz,2H),2.803(t,J＝6.8Hz,2H)；13C NMR(100MHz,DMSO)δ161.68,161.22,156.77,151.19,145.95,145.45,145.09,144.68,144.07,134.38,134.21,133.02,132.32,131.76,131.65,131.35,130.17,129.65,129.46,129.35,128.26,124.77,124.13,120.17,119.70,114.80,114.54,113.46,56.02,55.95,48.55,30.04,20.63。
实施例19：合成化合物BDP-19
化合物BDP-19的合成方法同化合物BDP-14合成路线，使用BDP-6(11.8mg，0.02mmol)，碘甲烷(0.30mL)，得到有红棕色金属光泽固体BDP-19(14mg，96％)。1H NMR(400MHz,DMSO)δ9.126(d,J＝6.2Hz,2H),8.467(d,J＝8.6Hz,1H),8.383(d,J＝6.2Hz,2H),8.015(d,J＝8.6Hz,2H),7.794(d,J＝4.9Hz,1H),7.680(d,J＝3.7Hz,1H),7.552(s,1H),7.255(t,J＝4.2Hz 1H),7.121(d,J＝6.9Hz,3H),7.039(s,1H),7.016(s,1H),4.413(s,3H),3.869(d,J＝6.4Hz,6H),2.888(dd,J＝43.1,6.6Hz,4H)；13C NMR(100MHz,DMSO)δ161.74,161.46,157.76,151.01,148.34,146.11,143.95,137.76,134.60,134.25,133.91,132.49,132.38,131.69,129.53,129.46,129.04,128.09,124.34,122.58,120.05,118.83,114.82,114.57,113.46,56.00,55.95,48.02,29.93,20.91。
实施例20：合成化合物BDP-20
化合物BDP-20的合成方法同化合物BDP-14合成路线，使用BDP-7(12.3mg，0.02mmol)，碘甲烷(0.30mL)，得到有红棕色金属光泽固体BDP-20(15mg，97％)。1H NMR(400MHz,DMSO)δ9.377(s,1H),9.063(d,J＝6.1Hz,1H),8.765(d,J＝8.1Hz,1H),8.610(dd,J＝23.8,8.9Hz,2H),8.287(t,J＝5.4Hz 1H),7.831(d,J＝5.1Hz,1H),7.521(d,J＝3.6Hz,1H),7.367(s,1H),7.288(t,J＝4.2Hz 1H),7.140–6.977(m,4H),4.443(s,3H),3.882(d,J＝4.3Hz,6H),2.999–2.744(m,8H)；13C NMR(100MHz,DMSO)δ161.93,161.21,152.98,149.10,145.88,145.37,144.91,144.35,143.37,135.54,133.64,132.71,132.66,130.58,130.37,130.09,129.96,129.82,129.35,129.07,128.29,120.72,120.64,120.24,114.91,114.85,113.47,113.29,56.03,55.94,48.60,30.22,30.16,21.29,20.56。
实施例21：合成化合物BDP-21
化合物BDP-21合成方法同化合物BDP-14合成路线，使用BDP-8(10.2mg，0.02mmol)，碘甲烷(0.30mL)，得到有紫色金属光泽固体BDP-21(12mg，92％)。1H NMR(400MHz,DMSO)δ9.090(d,J＝6.3Hz,2H),8.485(d,J＝6.5Hz,2H),8.235(d,J＝3.9Hz,1H),8.118(d,J＝5.0Hz,1H),7.967(dd,J＝8.0,1.6Hz,2H),7.918(d,J＝5.1Hz,1H),7.860(d,J＝2.8Hz,2H),7.595–7.513(m,4H),7.433(s,1H),7.342(dt,J＝13.8,4.7Hz,2H),4.373(s,3H).13C NMR(100MHz,DMSO)δ154.26,153.59,148.70,146.12,141.05,136.51,135.59,135.09,134.75,133.47,132.88,132.42,132.37,130.86,130.38,130.09,129.82,129.68,129.59,128.96,126.42,124.71,120.66,120.16,47.79。
实施例22：合成化合物BDP-22
化合物BDP-22的合成方法同化合物BDP-14合成路线，使用BDP-9(9.9mg，0.02mmol)，碘甲烷(0.30mL)，得到有紫色金属光泽固体BDP-22(10mg，99％)1H NMR(400MHz,DMSO)δ9.26(d,J＝5.9Hz,1H),8.75(t,J＝7.7Hz,1H),8.31(dd,J＝11.3,5.9Hz,2H),7.94(d,J＝7.9Hz,2H),7.81(d,J＝6.6Hz,2H),7.73(d,J＝6.5Hz,3H),7.62–7.56(m,4H),7.55–7.46(m,4H),7.37(s,1H),7.26–7.20(m,1H),7.14(dd,J＝15.4,7.4Hz,1H),4.22(s,3H)；13C NMR(100MHz,DMSO)δ163.55,150.41,147.82,146.92,145.79,142.56,139.24,137.81,137.69,132.86,132.04,131.96,131.89,131.54,131.00,130.68,130.58,130.00,129.88,129.67,129.63,129.37,129.25,129.15,129.01,128.67,125.78,122.43,119.01,47.50,21.52。
实施例23：合成化合物BDP-23
化合物BDP-23的合成方法同化合物BDP-14合成路线，使用BDP-10(10.5mg，0.02mmol)，碘甲烷(0.30mL)，得到有紫黑色金属光泽固体BDP-23(10.2mg，98％)1H NMR(400MHz,DMSO)δ9.44(s,1H),9.01(t,J＝7.6Hz,2H),8.30–8.25(t,1H),8.10(d,J＝8.9Hz,2H),7.78(d,J＝6.8Hz,2H),7.70(d,J＝7.2Hz,2H),7.57(q,J＝7.8Hz,6H),7.48(t,J＝7.3Hz,1H),7.39(s,1H),7.25(s,1H),7.13(d,J＝8.9Hz,2H),4.42(s,3H),3.87(s,3H).13CNMR(100MHz,DMSO)δ162.47,162.25,149.11,145.71,145.38,144.27,144.09,144.07,142.48,137.10,133.36,133.08,132.43,132.33,132.20,130.35,129.83,129.80,129.51,129.45,129.08,127.94,127.80,123.39,122.09,119.22,114.81,56.09,48.81。
实施例24：合成化合物BDP-24
化合物BDP-24的合成方法同化合物BDP-14合成路线，使用BDP-11(10.5mg，0.02mmol)，碘甲烷(0.30mL)，得到有紫色金属光泽固体BDP-24(10.2mg，98％)1H NMR(400MHz,DMSO)δ9.012(d,J＝6.9Hz,2H),8.675(d,J＝9.1Hz,1H),8.589(d,J＝6.9Hz,2H),7.664–7.500(m,10H),7.443(t,J＝7.3Hz,1H),7.288(s,1H),7.148(d,J＝2.5Hz,1H),7.064(dd,J＝9.0,2.6Hz,1H),4.335(s,3H),3.927(s,3H),3.011(t,J＝6.7Hz,2H),2.857(t,J＝7.3Hz,2H).13C NMR(100MHz,DMSO)δ163.87,159.50,147.35,146.76,145.56,142.90,141.97,139.71,139.36,134.68,134.33,133.22,130.98,130.11,129.88,129.67,129.58,129.04,125.52,125.46,125.41,122.99,121.01,118.99,114.92,114.37,56.30,55.37,47.66,30.00,21.08。
实施例25：合成化合物BDP-25
化合物BDP-25的合成方法同化合物BDP-14合成路线，使用BDP-12(10.5mg，0.02mmol)，碘甲烷(0.30mL)，得到有紫色金属光泽固体BDP-25(10.2mg，98％)1H NMR(400MHz,DMSO)δ9.509(s,1H),9.111(d,J＝8.3Hz,1H),9.061(d,J＝6.0Hz,1H),8.344(dd,J＝8.1,6.2Hz,1H),8.264(d,J＝3.3Hz,1H),8.138(d,J＝4.8Hz,1H),7.766(d,J＝6.4Hz,2H),7.709(d,J＝7.2Hz,2H),7.615–7.521(m,7H),7.491(t,J＝7.3Hz,1H),7.374(t,J＝4.4Hz,1H),7.328(s,1H),4.464(s,3H).13C NMR(100MHz,DMSO)δ154.01,148.73,145.82,145.38,144.40,143.97,143.91,143.84,142.51,137.03,135.59,135.08,135.03,134.97,133.71,133.05,132.55,132.25,131.96,130.39,129.83,129.78,129.50,129.47,129.11,127.92,126.98,121.68,119.41,48.89。
实施例26：合成化合物BDP-26
化合物BDP-26的合成方法同化合物BDP-14合成路线，使用BDP-13(10.2mg，0.02mmol)，碘甲烷(0.30mL)，得到有墨绿色金属光泽固体BDP-24(12mg，92％)。1H NMR(300MHz,DMSO)δ9.085(d,J＝6.3Hz,2H),8.485(d,J＝6.6Hz,2H),8.234(d,J＝3.5Hz,1H),8.121(d,J＝5.0Hz,1H),7.943(dd,J＝13.5,6.2Hz,3H),7.858(s,2H),7.653–7.471(m,4H),7.433(s,1H),7.341(dt,J＝10.4,4.5Hz,2H),4.361(s,3H).；13C NMR(75MHz,DMSO)δ156.34,151.76,150.53,141.14,140.40,139.05,135.46,134.12,133.47,133.16,132.83,132.72,132.61,132.36,130.60,129.71,129.52,129.48,129.41,128.61,128.37,128.23,127.63,124.28,123.16,119.03,118.70。
实施例27：化合物光学参数的测试
将所合成的化合物测试了在乙腈中的最大吸收波长(λabs)、摩尔消光系数(ε)、荧光发射波长(λem)、半峰宽、Stocks位移和荧光量子产率(Φf)，对应的数据在表1中列出。
表1 BODIPY染料的光谱性质
由表1可知，BDP母核结构引入吡啶基、噻吩基和并环结构使波长红移，BDP-14～BDP-26与BDP-1～BDP-13相比，季铵盐化后波长红移，摩尔消光系数下降，荧光量子产率降低，Stokes位移增大。
实施例28：成像测试
(1)细胞培养：实验选用HeLa细胞(人宫颈癌细胞)，培养基为DMEM(HyClone)，培养基含有10％胎牛血清(FBS)和1％的青霉素(10,000units/mL)-链霉素(10,000μg/mL)(HyClone)。细胞复苏后，在37℃含有5％CO2培养箱中培养。
(2)细胞成像：将每皿的量为300000个HeLa细胞接种到共聚焦成像培养皿，在37℃下，用含有10％小牛胚胎血清的DMEM培养液培养24h。把BDP-1(2.2mg BDP-1溶于4mlDMSO，再取20μL BDP-1的DMSO混合液到2ml DMEM中)的DMSO溶于与培养皿中的HeLa细胞在37℃下培养20分钟，用PBS洗涤三次，然后使用共聚焦显微镜成像，以不加BDP-1的DMSO混合液的培养皿作为对照，结果见图1。
如图1所示，(A)对照组荧光图像；(B)对照组明场与暗场图片重合图；(C)暗场中化合物BDP-1的红色荧光图像；(D)明场与暗场化合物BDP-1的红色荧光重合图。与对照组相比BDP-1能很好的在HeLa细胞中染色。
(3)线粒体靶向成像：将每皿的量为300000个HeLa细胞接种到共聚焦成像培养皿，在37℃下，用含有10％小牛胚胎血清的DMEM培养液培养24h。把BDP-14(10μM，2.8mg BDP-14溶于4ml DMSO，再取20μL BDP-14的DMSO混合液到2ml DMEM中)与培养皿中的HeLa细胞在37℃下培养20分钟，用PBS洗涤三次，洗掉多余BDP-14；然后把Mito-Tracker Green(200nM，取1μL Mito-Tracker Green到2ml DMEM中)与培养皿中的HeLa细胞在37℃下培养20分钟，用PBS洗涤三次，然后使用共聚焦显微镜成像，结果详见图2。
如图2所示，(A)明场中细胞形态；(B)Mito-Tracker Green(200nM)的绿色荧光图像；(C)化合物BDP-14的红色荧光图像；(D)图A，B和C的叠合图。从D图可以看出BDP-14具有良好的线粒体靶向能力。

Claims (6)

1.吡啶或吡啶季铵盐取代BODIPY类化合物，其特征在于，所述化合物具有下述通式(I)、(II)或(III)的结构：
其中：Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐，且Ar1、Ar2和Ar3至少一个为下述中的一种：吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐；所述季铵盐为甲基吡啶季铵盐、乙基吡啶季铵盐或苄基吡啶季铵盐，其阴离子为溴负离子、碘负离子或三氟甲磺酸负离子；
R1、R2独立地选自H、C1-C3烷基、C1-C3烷氧基、F、Cl、Br或OH；
所述Ar1、Ar2、Ar3中为带有取代基的吡啶环或其季铵盐时，取代基任选自以下基团：F、Cl、Br、羟基、氨基、硝基、氰基、三氟甲基、三氟甲氧基、C1-C3烷基或C1-C3烷氧基。
2.根据权利要求1吡啶或吡啶季铵盐取代BODIPY类化合物，其特征在于，Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐，且Ar1、Ar2或Ar3至少一个为下述中的一种：吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐；所述季铵盐为甲基吡啶季铵盐、乙基吡啶季铵盐，其阴离子为溴负离子或碘负离子；R1、R2独立地选自H、甲基、甲氧基、F、Cl、Br或OH；所述Ar1、Ar2、Ar3中可带有F、Cl、Br、甲基或甲氧基。
3.根据权利要求1吡啶或吡啶季铵盐取代BODIPY类化合物，其特征在于，其中Ar1、Ar2及Ar3独立地选自取代或未取代的苯基、取代或未取代的噻吩基、取代或未取代的呋喃基、吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐，且Ar1、Ar2或Ar3至少一个为下述中的一种：吡啶-2-基或其季铵盐、吡啶-3-基或其季铵盐、吡啶-4-基或其季铵盐；所述季铵盐为甲基吡啶季铵盐，其阴离子为碘负离子；R1、R2独立地选自H、甲基或甲氧基；所述Ar1、Ar2、Ar3中可带有取代基，任选自以下基团：F、Cl、Br、羟基或甲氧基。
4.根据权利要求1吡啶或吡啶季铵盐取代BODIPY类化合物，其特征在于，具体为下列化合物：
5.权利要求1-4任一项吡啶或吡啶季铵盐取代BODIPY类化合物在制备荧光成像剂中的应用。
6.根据5所述的应用，其特征在于，所述荧光成像剂为细胞荧光成像剂。
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WO2024075649A1 (ja) * 2022-10-07 2024-04-11 東レ株式会社 ピロメテンホウ素錯体、色変換組成物、色変換シート、色変換基板、光源ユニット、表示装置および照明装置

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* Cited by examiner, † Cited by third party
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WO2024075649A1 (ja) * 2022-10-07 2024-04-11 東レ株式会社 ピロメテンホウ素錯体、色変換組成物、色変換シート、色変換基板、光源ユニット、表示装置および照明装置

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