CN110028427A - 含有9,10-双（二苯基亚甲基）蒽结构的压致荧光变色材料及其在压力检测中的应用 - Google Patents
含有9,10-双（二苯基亚甲基）蒽结构的压致荧光变色材料及其在压力检测中的应用 Download PDFInfo
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Abstract
一种含有9,10‑双(二苯基亚甲基)蒽结构单元的压致荧光变色材料及其在压力检测中的应用，属于荧光材料技术领域。本发明在9,10‑双(二苯基亚甲基)蒽结构单元的外围苯环的对位上引入四个氰基，使化合物晶体中形成松散而有序的排列方式，具有优异的高压下压致变色性能。其晶体的荧光发射峰位与外界压力的大小呈现线性关系，可通过荧光峰位的变化定量检测0‑14.7GPa范围内的外界压力，伴随荧光光谱上138nm的红移，检测的灵敏度为9.62nm GPa‑1，可实现对压力的定量检测。
Description
技术领域
本发明属于荧光材料技术领域，具体涉及一种含有9,10-双(二苯基亚甲基) 蒽结构单元的压致荧光变色材料，该压致变色荧光材料晶体的荧光发射峰位与外界压力的大小呈现线性关系，可通过荧光峰位的变化定量检测0～14.7GPa范围内的外界压力。
背景技术
有机压致荧光变色材料用途广泛，它不仅可以作为传感器、信息显示器和存储器等被应用于显示屏、安保系统和记录器中，它还可应用于多种新兴的领域，比如保密信纸、安全墨水等等。随着科学的发展和社会的进步，人们对可承受较高压力的具有特殊用途的有机小分子压致荧光变色材料的需求进一步增加，它们可用大型飞机风洞实验，压力传感器等领域。因此开发出新型可在高压下表现出压致荧光变色功能的材料具有重要意义。
有机小分子荧光材料作为传感器具有灵敏度高、响应时间短、可视性等优点。如果用压致荧光变色材料作为压力荧光传感器，必须满足两个条件：一是明显的荧光颜色改变，二是高的灵敏度。目前虽然已有一些关于高压下具有压致荧光变色材料的报道，但是由于缺乏对此类分子构效关系的深入研究和高压下压致变色有机小分子设计理论的缺失，导致了此类分子的设计较为困难，而对于如何提高有机小分子在高压下的灵敏度更是未见报道。
具有确定分子量的高纯度9,10-双(二苯基亚甲基)蒽类化合物，是一种具有良好荧光性能的结构单元，对具有9,10-双(二苯基亚甲基)蒽结构的衍生物的聚集诱导发光性能和压致变色性能的研究非常多，但是对于具有9,10-双(二苯基亚甲基)蒽结构单元的分子的在高压条件下的压致荧光变色材料方面研究尚未见报道。近两年，有相关研究报道，如唐本忠教授课题组设计、制备了基于给体-受体原理的具有聚集诱导发光性能的在常压下具有压致荧光变色性质的材料 (Zikai He,Liuqing Zhang,Ju Mei,Tian Zhang,JackyW.Y.Lam,Zhigang Shuai, Yong Qiang Dong,Ben Zhong Tang,Chem.Mater.2015,27,6601-6607)。然而，这一类的压致荧光变色材料在高压下的性质研究非常稀少。能够实现定量检测外界压力的9,10-双(二苯基亚甲基)蒽类化合物材料更是未见报道。
发明内容
针对已有技术的不足，本发明的目的在于提供一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料，其具有良好的光学稳定性，可用于压力传感方面，具有良好的颜色对比度和灵敏性。
本发明所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料，其结构式如下所示：
本发明通过将刚性9,10-双(二苯基亚甲基)蒽大分子平面与二氰基二苯基相连，外围苯环的对位上引入四个氰基，引入较大的空间位阻效应，使分子间形成松散而有序的排列方式，所得的材料M1具有优异的高压下变色性能。其反应式如下所示：
与现有技术相比，本发明具有以下有益效果：
(1)本发明将具有优异荧光性能的9,10-双(二苯基亚甲基)蒽与二氰基二苯基结构单元应用到高压下具有压致荧光变色材料领域，设计、合成了目标化合物，对其进行荧光性能和高压下压致变色性能的表征，扩展了其潜在应用范围。
(2)化合物可承受14.7GPa的高压，荧光波长的变化与外界压力的大小呈现线性关系，可实现对压力的定量检测，且具有良好的灵敏度。
附图说明
图1是本发明实施例1中化合物M1晶体从常压到逐步加高压至14.7GPa 前后吸收光谱图。
图2是本发明实施例1中化合物M1晶体从常压到逐步加高压至14.7GPa 前后荧光光谱图。
图3是本发明实施例1中化合物M1晶体从常压到逐步加高压至14.7GPa 前后荧光颜色对照图。随着压力从0增加至14.7GPa,M1晶体的荧光下发光颜色也从未加压力时的灰白色逐渐变至红色，亮度也随之逐渐变暗,至14.7GPa 时几乎看不到发光亮度。
图4是本发明实施例1中化合物M1晶体检测压力的灵敏度图。
具体实施方式
下面结合实施例1，对本发明做进一步的详细说明。
实施例1：
M1其制备方法，包括以下步骤：
取9,10-二(二溴亚甲基)-9,10-二氢9,10-双(二苯基亚甲基)蒽(519.86mg,1mmol)，4-硼酸氰基苯(1.18g,8.0mmol)，无水碳酸钾(2.21g,16.0mmol)，精制甲苯12mL，无水乙醇6mL和去离子水8mL加入到100mL单颈圆底烧瓶中，加入催化剂四(三苯基膦)钯(92.40mg,0.08mmol)，在氮气环境下升温至110℃反应48h。反应结束后，用二氯甲烷萃取有机相并旋干得到粗产品，以石油醚和二氯甲烷的混合溶剂(二者体积比为4:1)作为展开剂用柱层析分离得到黄色化合物M1 413.4mg，产率为68％。M1的核磁氢谱数据为1H NMR(500MHz, DMSO):δ(ppm)7.87(d,J＝8.0Hz,8H),7.80(d,J＝8.0Hz,8H),6.91–6.89(m,4H),6.87–6.83(m,4H)。
M1晶体制备方法：
取4mg M1粉末完全溶解在4mL良溶剂并置于干净干燥的10mL试管里，并在溶液上方缓慢加入1mL不良溶剂，然后用一小团棉花紧紧堵住试管开口处，再将试管放入500mL干净广口瓶中，并在广口瓶中加入100mL不良溶剂，同时在广口瓶外侧包裹锡纸来避光。将广口瓶静置在室温环境下7天，可得到若干稳定的黄色方块状晶体。其中试管中良溶剂可选二氯甲烷、三氯甲烷、四氢呋喃等溶剂，试管中和广口瓶中的不良溶剂可选无水甲醇、无水乙醇等溶剂。
实施例2：高压传感性能展示
选取M1晶体的晶粒大小在0.2mm×0.4mm×0.2mm为最佳，放入金刚石对顶砧装置，以红宝石为压力探测器，硅油为传压介质进行高压实验。如附图1 所示，在高压吸收光谱中，随着压力逐渐增大，当压力达到14.9GPa时，吸收带边由初始状态下416nm红移到了762nm，吸收带隙从3.0eV变化到1.6eV。如附图2所示，在高压荧光光谱中，稍一加压到0.2GPa，晶体颜色会迅速发生变化，且荧光强度降低，当压力增大至14.7GPa，晶体颜色已经由灰白色变至红色(附图3)，同时荧光光谱红移到了655nm，颜色变化138nm。如附图4所示，以加压过程中M1晶体的发射光谱峰位为纵坐标，压力为横坐标作图，荧光峰位的变化相对于压力的变化呈现线性关系，利用公式(λ为荧光峰位波长，P为压力)计算图4的斜率，其中Pn-1为初始外界压力值,可以是附图4 上的线性拟合线上任意一点所对应的横坐标上的压力值,Pn为变化后的外界压力值,可以是附图4上的线性拟合线上,在Pn-1所对应的点之后的任意一点的横坐标上的压力值,λn-1是外界压力为Pn-1时对应的荧光峰位,λn是外界压力为Pn时对应的荧光峰位,该拟合线的斜率即为高压检测过程中的压制变色灵敏度,通过上述公式计算数值为9.62nm GPa-1。
虽然本发明以上实施例公开如上，但其并非用以限定本发明的保护范围，任何熟悉该技术的技术人员，在不脱离本发明的构思和范围内所作的更改与润饰，均应属于本发明的保护范围。
Claims (4)
1.一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料，其结构式如下所示：
2.权利要求1所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料在压力检测中的应用。
3.如权利要求2所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料在压力检测中的应用，其特征在于：压致荧光变色材料晶体的荧光发射峰位与外界压力的大小呈现线性关系，用于检测0-14.7GPa的外界压力。
4.如权利要求2所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料在压力检测中的应用，其特征在于：灵敏度为9.62nm GPa-1。
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