CN109096284B - 一种具有双光子吸收特性的有机化合物及其制备方法和应用 - Google Patents
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Abstract
本发明提供一种具有双光子吸收特性的有机化合物及其制备方法和应用,属于有机化合物合成技术领域。该有机化合物以萘四胺和二芳基邻苯二酮为原料,采用脱水缩合反应制备,制备方法简单,条件温和,同时制备得到的有机化合物经过组装成双光子器件后,测试发现采用800nm波长激发后,最大双光子吸收截面增大为702GM,从而极大地提高了其在光电领域应用范围。
Description
技术领域
本发明属于有机化合物合成技术领域,具体涉及一种具有双光子吸收特性的有机化合物及其制备方法和应用。
背景技术
该部分内容仅提供与本发明有关的背景信息,并不必然构成现有技术。
氮杂稠环芳烃及其衍生物是一种具有优异物理及化学性质的平面共轭稠环大分子。因其独特的光物理性质和电化学性质及在常见有机溶剂中优异的溶解性使得它在有机太阳能转化、光导体、信号放大、激光染料、荧光探针、荧光聚集体、液晶材料等许多领域有着广泛的应用前景。
双光子吸收是一种光学非线性效应,它是指一个原子或分子同时吸收两个不同频率的光子后,从低能级向高能级跃迁的过程。近年来,伴随着分子工程和有机合成技术的发展,具有大的双光子吸收截面的有机分子逐渐被发现,由于有机双光子吸收材料具有构成器件结构简单,使用方便,瞬间响应快,线性透射率高,可裁剪等优点,人们逐渐将目光由无机材料转向有机材料。随着大量双光子吸收材料的设计与合成,双光子吸收在双光子荧光显微镜,激光上转换,光限幅,高密度数据存储、单分子检测、医疗诊断以及三维微加工和光动力诊疗等等高科技领域引起了国内外学者的高度关注。
然而,现有技术文献中基于氮杂稠环芳烃及其衍生物的双光子吸收截面较低,不超过200GM,因此极大地限制了氮杂稠环芳烃及其衍生物在光电领域的应用。
发明内容
针对上述技术不足和技术空缺,发明人经长期的技术与实践探索,发现了一类基于氮杂稠环芳烃为核心,芳环作为取代基的新型具有双光子吸收特性的有机化合物,该有机化合物以萘四胺和邻苯二酮为原料,采用脱水缩合反应制备,制备方法简单,条件温和,同时制备得到的有机化合物经过组装成双光子器件后,测试发现采用800nm波长激发后,最大双光子吸收截面增大为702GM,从而极大地提高了其在光电领域应用范围。
本发明的目的之一在于提供一种具有双光子吸收特性的有机化合物。
本发明的目的之二在于提供上述有机化合物的制备方法。
本发明的目的之三在于提供上述有机化合物的应用。
为实现上述目的,本发明涉及以下技术方案:
本发明的第一个方面,提供一种具有双光子吸收特性的有机化合物,所述具有双光子吸收特性的有机化合物具有如下通式结构:
式I和II中的R代表氢原子、烷基和烷基乙炔基硅;
优选的,R代表氢原子、C1~C20的烷基乙炔基硅;
进一步优选的,R代表三异丙基硅基乙炔(TIPS);
本发明的第二个方面,提供上述具有双光子吸收特性的有机化合物的制备方法,所述方法包括将二芳基邻二酮基化合物与萘四胺化合物通过脱水缩合反应制备得到所述具有双光子吸收特性的有机化合物的步骤。
其中,所述二芳基邻二酮基化合物包括但不限于二苯基邻二酮基化合物和/或二噻吩基邻二酮基化合物;
所述萘四胺化合物为1,2,5,6-萘四胺;
进一步的,所述具有双光子吸收特性的有机化合物的制备方法包括:
在无水无氧条件下,将二芳基邻二酮基化合物与萘四胺化合物溶于有机溶剂中,然后升温进行脱水缩合反应得到有机化合物。
其中,二芳基邻二酮基化合物与萘四胺化合物的摩尔比为1:1~10;
所述二芳基邻二酮基化合物包括但不限于二苯基邻二酮基化合物、二噻吩基邻二酮基化合物;
所述萘四胺化合物包括1,2,5,6-萘四胺;
所述有机溶剂优选为无水吡啶;
反应温度为120~140℃,进一步优选为130℃;
反应时间为10~14h,进一步优选为12h。
本发明的第三个方面,提供所述具有双光子吸收特性的有机化合物在光学非线性材料、光导体、信号放大材料、激光染料、荧光探针、荧光聚集体或液晶材料中的应用。
本发明的有益效果:
(1)本发明首次采用脱水缩合反应基于氮杂稠环芳烃和取代苯环作为取代基制备出一种全新的有机化合物,同时制备得到的有机化合物经过组装成双光子器件后,测试发现采用800nm波长激发后,最大双光子吸收截面增大为702GM,从而极大地提高了其在光电领域应用范围,在光电领域具有巨大的潜在应用价值;
(2)本发明反应原料廉价易得,反应条件温和,步骤简单,处理方便、污染少;同时反应产率较高,其中,产率高达80%以上,便于工业化规模生产。
附图说明
图1为本发明实施例1制备产品的核磁氢谱图;
图2为本发明实施例1制备产品的质谱图;
图3为本发明实施例1制备产品的非线性光谱图,其中,图3a是开孔情况下飞秒Z扫描曲线图;图3b是闭孔情况下飞秒Z扫描曲线图;
图4为本发明实施例2制备产品的核磁氢谱图;
图5为本发明实施例2制备产品的质谱图;
图6为本发明实施例2制备产品的非线性光谱图,其中,图6a是开孔情况下飞秒Z扫描曲线图;图6b是闭孔情况下飞秒Z扫描曲线图。
具体实施方式
应该指出,以下详细说明都是例示性的,旨在对本申请提供进一步的说明。除非另有指明,本文使用的所有技术和科学术语具有与本申请所属技术领域的普通技术人员通常理解的相同含义。
需要注意的是,这里所使用的术语仅是为了描述具体实施方式,而非意图限制根据本申请的示例性实施方式。如在这里所使用的,除非上下文另外明确指出,否则单数形式也意图包括复数形式,此外,还应当理解的是,当在本说明书中使用术语“包含”和/或“包括”时,其指明存在特征、步骤、操作、器件、组件和/或它们的组合。
如前所述,现有技术文献中基于氮杂稠环芳烃及其衍生物的双光子吸收截面较低,不超过200GM,因此极大地限制了氮杂稠环芳烃及其衍生物在光电领域的应用。
本发明的一种典型实施方式中,提供了一种基于氮杂稠环芳烃为核心,芳环作为取代基的新型具有双光子吸收特性的有机化合物,该有机化合物具有如下通式结构:
其中,
式I和II中的R代表氢原子、烷基和烷基乙炔基硅;
优选的,R代表氢原子、C1~C20的烷基乙炔基硅;
进一步优选的,R代表三异丙基硅基乙炔(TIPS);
本发明的又一典型实施方式中,提供了所述基于氮杂稠环芳烃为核心,芳环作为取代基的新型的具有双光子吸收特性的有机化合物的制备方法,所述方法包括将二芳基邻二酮基化合物与萘四胺化合物通过脱水缩合反应制备得到有机化合物的步骤;
其中,所述二芳基邻二酮基化合物包括二苯基邻二酮基化合物或二噻吩基邻二酮基化合物;
萘四胺化合物为1,2,5,6-萘四胺化合物;
本发明的又一典型实施方式中,所述基于氮杂稠环芳烃为核心,芳环作为取代基的新型有机双光子吸收化合物的制备方法如下:
在无水无氧条件下,将二芳基邻二酮基化合物与萘四胺化合物溶于有机溶剂中,然后升温进行脱水缩合反应得到有机化合物。
本发明的又一典型实施方式中,二芳基邻二酮基化合物与萘四胺化合物的摩尔比为1:1~10;
本发明的又一典型实施方式中,二芳基邻二酮基化合物指的是二苯基邻二酮基化合物与二噻吩基邻二酮基化合物;
本发明的又一典型实施方式中,
所述二苯基邻二酮基化合物为1,1-二(三异丙基硅基乙炔)二苯基乙二酮;
所述二噻吩基邻二酮基化合物为2,2’-二(三异丙基硅基乙炔)二噻吩乙二酮;
本发明的又一典型实施方式中,萘四胺化合物为1,2,5,6-萘四胺;
本发明的又一典型实施方式中,有机溶剂优选为无水吡啶;
本发明的又一典型实施方式中,反应温度为120~140℃,进一步优选为130℃;
本发明的又一典型实施方式中,反应时间为10~14h,进一步优选为12h。
本发明的又一典型实施方式中,提供了有机化合物在光学非线性材料、光导体、信号放大材料、激光染料、荧光探针、荧光聚集体、液晶材料中的应用。
下面通过实施例,对本发明的操作,作进一步具体的说明。
实施例1
将100mL的反应瓶抽真空并通氮气保护,称取200mg 1,2,5,6-萘四胺(1)和750mg,1,1-二(三异丙基硅基乙炔)二苯基乙二酮(2),30mL的无水吡啶,加入反应瓶中,开启油浴锅加热至130℃,反应经过12小时后结束,所得粗产品经过薄层色谱分离提纯得到浅黄色产品(3)0.6g,产率80%。
实施例2
将100mL的反应瓶抽真空并通氮气保护,称取200mg 1,2,5,6-萘四胺(1)和750mg,2,2’-二(三异丙基硅基乙炔)二噻吩乙二酮(4),30mL的无水吡啶,加入反应瓶中,开启油浴锅加热至130℃,反应经过12小时后结束,所得粗产品经过薄层色谱分离提纯得到浅黄色产品(5)0.70g,产率90%。
制备产品非线性光学特性参数
制备得到的有机化合物经过组装成双光子器件后,测试发现采用800nm波长激发后,化合物3的非线性光谱图如图3所示,经测算其最大双光子吸收截面增大为702GM,化合物5的非线性光谱图如图6所示,经测算后其最大双光子吸收截面增大为592GM,这是目前报道的基于氮稠杂类化合物最高的数值,从而极大地提高了其在光电领域应用范围。
应注意的是,以上实例仅用于说明本发明的技术方案而非对其进行限制。尽管参照所给出的实例对本发明进行了详细说明,但是本领域的普通技术人员可根据需要对本发明的技术方案进行修改或者等同替换,而不脱离本发明技术方案的精神和范围。
Claims (8)
3.权利要求2所述的具有双光子吸收特性的有机化合物的制备方法,其特征在于,所述制备方法如下:
在无水无氧条件下,将二芳基邻二酮基化合物与萘四胺化合物溶于有机溶剂中,然后升温进行脱水缩合反应得到有机化合物。
4.如权利要求3所述的具有双光子吸收特性的有机化合物的制备方法,其特征在于,二芳基邻二酮基化合物与萘四胺化合物的摩尔比为1:1~10。
5.如权利要求3所述的具有双光子吸收特性的有机化合物的制备方法,其特征在于,有机溶剂为无水吡啶。
6.如权利要求3所述的具有双光子吸收特性的有机化合物的制备方法,其特征在于,反应温度为120~140℃;反应时间为10~14h。
7.如权利要求6所述的具有双光子吸收特性的有机化合物的制备方法,其特征在于,反应温度为130℃;反应时间为12h。
8.权利要求1所述的有机化合物或权利要求2-7任一项所述制备方法制备得到的有机化合物在光学非线性材料、光导体、信号放大材料、激光染料、荧光探针、荧光聚集体、液晶材料中的应用。
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