CN111087403B - 一种具有红色聚集诱导发光特性的卟啉衍生物及其制备方法和应用 - Google Patents

一种具有红色聚集诱导发光特性的卟啉衍生物及其制备方法和应用 Download PDF

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CN111087403B
CN111087403B CN201911111788.2A CN201911111788A CN111087403B CN 111087403 B CN111087403 B CN 111087403B CN 201911111788 A CN201911111788 A CN 201911111788A CN 111087403 B CN111087403 B CN 111087403B
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卢小泉
张银潘
邴勇博
王铁英
白蕾
韩振刚
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Abstract

本发明公开了一种具有红色聚集诱导发光特性的卟啉衍生物；及其制备方法和应用。通过四苯基乙烯基团修饰卟啉分子，由于四苯基乙烯“螺旋桨”状非平面结构的引入，在空间结构上极大的降低卟啉分子间的π‑π堆积作用，使卟啉从聚集荧光淬灭转变为聚集诱导发光；该卟啉衍生物能够在聚集态和固体时发射强烈的红色荧光，能够在有机电致发光器件及近红外生物成像领域取得很好的应用。

Description

一种具有红色聚集诱导发光特性的卟啉衍生物及其制备方法 和应用
技术领域
本发明属于发光材料技术领域，具体涉及一种具有红色聚集诱导发光特性的卟啉衍生物及其制备方法和应用。
背景技术
卟啉类化合物广泛存在于自然界的生命体内，如叶绿素、血红素和细胞色素等都是卟啉衍生物，在生命活动中发挥着重要作用。卟啉是一类具有18π电子共轭的刚性平面大分子杂环化合物，在可见光范围内具有强的吸收和发射性质。卟啉及其衍生物已广泛应用于金属离子分析检测、生物成像、液晶材料、有机电致发光材料和染料敏化太阳能电池等领域。
但是卟啉类化合物在较高浓度或固态下，由于刚性平面共轭结构，分子间存在强烈的π-π相互作用而紧密堆积，导致荧光猝灭；卟啉类化合物具有独特的光电性质，采用卟啉掺杂的有机电致发光材料已成为研究热点；由于卟啉分子间的聚集导致荧光猝灭，使得单一卟啉作为发光二极管很难实现，因此在发光器件方面的应用受到了限制。为解决这一问题，开发卟啉聚集态发光很有必要。聚集诱导发光 (Aggregation Induced Emission,AIE)现象由唐本忠课题组2001年首次发现，噻咯和四苯基乙烯是典型的AIE分子，这类化合物与卟啉发光现象完全相反，在聚集态和固体时能够发射很强的荧光，为解决有机发光材料聚集荧光猝灭问题提供了新策略。
发明内容
本发明的第一个目的是为了解决上述问题，提供了一种具有红色聚集诱导发光特性的卟啉衍生物。
本发明的第二个目的是提供上述卟啉衍生物的制备方法。
本发明的第三个目的是提供上述卟啉衍生物的用途。
本发明的目的通过以下技术方案来具体实现：
一种具有红色聚集诱导发光特性的卟啉衍生物，结构式如下所示：
Figure BDA0002272929530000021
上述具有红色聚集诱导发光特性的卟啉衍生物的制备方法，具体包括如下步骤：
(1)制备5-(4-氨基苯基)-10,15,20-三苯基卟啉
首先采用Adler法合成四苯基卟啉，然后将四苯基卟啉溶于三氟乙酸，在低温条件下加入亚硝酸盐进行硝化反应，反应结束后，纯化分离得5-(4-硝基苯基)-10,15,20-三苯基卟啉，再在浓盐酸溶液中加入无机盐还原剂进行还原，加热回流，纯化分离得5-(4-氨基苯基)-10,15,20-三苯基卟啉；
(2)制备[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯
将1-(4-溴苯基)-1,2,2-三苯基乙烯和4-甲酰基苯硼酸通过Suzuki 偶联反应，合成[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯；
(3)制备聚集诱导发光卟啉衍生物
将5-(4-氨基苯基)-10,15,20-三苯基卟啉和[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯通过Schiff反应，得到四苯基乙烯基团修饰的卟啉衍生物。
进一步的，步骤(1)中，所述低温条件为-15℃，所述亚硝酸盐为亚硝酸钠，硝化反应的时间为30min；所述无机盐还原剂为 SnCl2·2H2O；加热回流在80℃下回流12h。
进一步的，步骤(3)中，5-(4-氨基苯基)-10,15,20-三苯基卟啉和 [1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯的摩尔比为1:2。
上述卟啉衍生物在有机电致发光、生物成像材料中的应用。
本发明通过四苯基乙烯分子共价连接卟啉，能够实现卟啉化合物在聚集态和固态下发射红色荧光，使卟啉从聚集荧光猝灭转变为AIE 性质。该材料可广泛应用于有机电致发光等领域。
本发明具有以下有益效果：
本发明提供的具有红色聚集诱导发光特性的卟啉衍生物，通过四苯基乙烯基团修饰卟啉分子，由于四苯基乙烯“螺旋桨”状非平面结构的引入，在空间结构上极大的降低卟啉分子间的π-π堆积作用，使卟啉从聚集荧光淬灭转变为聚集诱导发光；该卟啉衍生物能够在聚集态和固体时发射强烈的红色荧光，能够在有机电致发光器件及近红外生物成像领域取得很好的应用。
附图说明
图1中 (a)为实施例1合成的卟啉衍生物在含水量90％的DMF溶液中形成聚集体的发光照片，图1中 (b)为实施例1合成的卟啉衍生物固体粉末在紫外光365nm照射下发光照片。
图2为实施例1合成的聚集诱导发光卟啉衍生物1H-NMR谱图。
图3为实施例1合成的聚集诱导发光卟啉衍生物(曲线a)和氨基卟啉(曲线b)的紫外-可见吸收光谱。
图4为实施例1合成的聚集诱导发光卟啉衍生物(曲线a)和氨基卟啉(曲线b)在含水量90％的DMF溶液中聚集体状态下的荧光发射光谱。
具体实施方式
以下对本发明的优选实施例进行说明，应当理解，此处所描述的优选实施例仅用于说明和解释本发明，并不用于限定本发明。
本发明的一种具有聚集诱导发光效应的卟啉衍生物材料，其结构式如下：
Figure BDA0002272929530000051
为了更清楚地说明本发明的内容，下面结合附图和具体的实施例对本发明再做进一步的说明，制备卟啉衍生物所用到的原料均为市场可得产品。
实施例1
(1)制备5-(4-氨基苯基)-10,15,20-三苯基卟啉
首先采用Adler法合成四苯基卟啉(TPP)，将苯甲醛(5mL， 50mmol)溶于80mL丙酸，在70℃逐滴加入吡咯(4.2mL，60mmol) 的丙酸溶液20mL，升温140℃回流搅拌1h，冷却后抽滤得TPP紫色晶体1.5g，产率20％。进一步将TPP(1.2g，2mmol)溶于三氟乙酸，在低温条件下(-15℃)加入亚硝酸钠(173mg，2.5mmol)硝化，反应30min结束，用二氯甲烷萃取，旋蒸除去溶剂得粗产物，柱层析分离得5-(4-硝基苯基)-10,15,20-三苯基卟啉1.1g，产率70％，进一步将 5-(4-硝基苯基)-10,15,20-三苯基卟啉(1g，1.26mmol)溶解于12mol/L 的浓盐酸溶液中，加入SnCl2·2H2O(1.4g，6.3mmol)进行还原，在 80℃加热回流12h，用氨水猝灭反应，用二氯甲烷萃取，旋蒸除去溶剂得粗产物，柱层析分离得5-(4-氨基苯基)-10,15,20-三苯基卟啉 780mg，产率92％。
Figure BDA0002272929530000061
(2)制备[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯
将1-(4-溴苯基)-1,2,2-三苯基乙烯(411mg，1mmol)、4-甲酰基苯硼酸(600mg，4mmol)和无水碳酸钾(0.7g，5mmol)溶于80mL甲苯，通氩气30min后加入Pd(PPh3)4(35mg，0.03mmol)，在氩气保护下回流搅拌24h，反应结束后加50mL水，用二氯甲烷萃取，有机相干燥后除去溶剂，粗产物经柱层析分离得[1-(4-甲醛基联苯基)-1,2,2- 三苯基]乙烯浅黄色固体395mg，产率90％。
Figure BDA0002272929530000062
(3)制备聚集诱导发光卟啉衍生物
将5-(4-氨基苯基)-10,15,20-三苯基卟啉(45mg，0.07mmol)和 [1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯(62.4mg，0.14mmol)溶于 60mL甲苯:乙醇(v:v＝2:1)混合溶剂，加入10μL乙酸，在氩气保护下回流搅拌48h，反应结束后过滤，除去溶剂，用乙醇反复洗涤并重结晶，得到四苯基乙烯基团修饰的卟啉衍生物砖红色固体64mg，产率68％。
Figure BDA0002272929530000071
核磁解析数据,1H-NMR(400MHz,CDCl3)δ8.94(d,J＝4.7Hz, 2H),8.88(d,J＝10.2Hz,7H),8.59(s,1H),8.30-8.22(m,9H),8.13(d, J＝8.3Hz,2H),7.79(t,J＝6.9Hz,11H),7.66(d,J＝8.2Hz,2H),7.50(d, J＝8.2Hz,2H),7.21-7.13(m,17H),-2.72(s,2H).
实施例2
实施例1合成的四苯基乙烯基团上修饰的卟啉衍生物固体粉末在紫外光365nm照射下发射强烈的红色荧光。将所制备的样品配置成0.5mM的DMF溶液，取0.1mL该溶液，加入0.9mL去离子水，制备成含水量为90％的聚集体溶液，该聚集体溶液在紫外光365nm 照射下发射强烈红色荧光。
由图3可以看出通过四苯基乙烯修饰后的卟啉在紫外光的范围吸收明显增强，且卟啉四个Q带吸收峰依次增强。
由图4可以看出氨基卟啉在聚集状态下几乎无荧光，由四苯基乙烯修饰后的卟啉衍生物在聚集状态下荧光明显增强
以上所述仅为本发明的优选实施例而已，并不用于限制本发明，尽管参照前述实施例对本发明进行了详细的说明，对于本领域的技术人员来说，其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换。凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (4)

1.一种具有红色聚集诱导发光特性的卟啉衍生物，结构式如下所示：
Figure FDA0002272929520000011
2.权利要求1所示的具有红色聚集诱导发光特性的卟啉衍生物的制备方法，其特征在于，具体包括如下步骤：
(1)制备5-(4-氨基苯基)-10,15,20-三苯基卟啉
首先采用Adler法合成四苯基卟啉，然后将四苯基卟啉溶于三氟乙酸，在低温条件下加入亚硝酸盐进行硝化反应，反应结束后，纯化分离得5-(4-硝基苯基)-10,15,20-三苯基卟啉，再在浓盐酸溶液中加入无机盐还原剂进行还原，加热回流，纯化分离得5-(4-氨基苯基)-10,15,20-三苯基卟啉；
(2)制备[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯
将1-(4-溴苯基)-1,2,2-三苯基乙烯和4-甲酰基苯硼酸通过Suzuki偶联反应，合成[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯；
(3)制备聚集诱导发光卟啉衍生物
将5-(4-氨基苯基)-10,15,20-三苯基卟啉和[1-(4-甲醛基联苯基)-1,2,2-三苯基]乙烯通过Schiff反应，得到四苯基乙烯基团修饰的卟啉衍生物。
3.根据权利要求2所述的具有红色聚集诱导发光特性的卟啉衍生物的制备方法，其特征在于，步骤(1)中，所述低温条件为-15℃，所述亚硝酸盐为亚硝酸钠，硝化反应的时间为30min；所述无机盐还原剂为SnCl2·2H2O；加热回流在80℃下回流12h。
4.权利要求1所述的卟啉衍生物在有机电致发光、生物成像材料中的应用。
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