CN109053779A - 一类力致变色材料及其制备方法 - Google Patents

一类力致变色材料及其制备方法 Download PDF

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CN109053779A
CN109053779A CN201810703845.5A CN201810703845A CN109053779A CN 109053779 A CN109053779 A CN 109053779A CN 201810703845 A CN201810703845 A CN 201810703845A CN 109053779 A CN109053779 A CN 109053779A
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刘美芳
李考学
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王林同
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Abstract

一类力致变色材料及其制备方法，所述的力致变色材料是具有通式I结构的化合物。本发明所提供的化合物具有研磨变色特性，从610nm红移到了653nm，在研磨‑熏蒸和研磨‑加热过程中，由于分子在晶态和无定型之间变化，导致发光颜色可逆转变；鉴于该类材料的良好的力致变色性质，可以对聚合物进行掺杂，检测聚合物材料在使用过程中的损伤和老化。

Description

一类力致变色材料及其制备方法
技术领域
本发明涉及一类新型的力致变色材料。
背景技术
近十年来，力致变色材料成为科学家们研究的热点，分子通常都具有大的空间位阻或扭转角，聚集态下，分子结构内螺旋桨状的非平面构象可以阻碍化合物在聚集态下的π-π堆积，使分子具有疏松的堆积结构，当受到外界刺激(如机械力，pH等)，常会随着分子间作用力的改变或构象的改变表现出荧光性质的变化，因而具有力致变色响应的特性。2010年，Park课题组首先报道了有聚集诱导发光(AIE)性质的二苯乙烯腈衍生物，在压力作用下化合物由绿色变为蓝色。将化合物掺杂在PMMA里面，这种薄膜显示出了快速响应和多种刺激变换的特性；2011年，Dibenzocarbazolediimides:Synthesis,Solid Structure,Self-Assembly Behavior,and Optoelectronic Properties(Physi.Chem.Lett,2011,2,666)报导合成了具有D-A结构的化合物BPPQ-TFM，它的荧光转化可以在多种刺激下响应，例如机械力、有机溶剂的熏蒸、热酸、碱等，荧光颜色从橙红色到黄色的转变；2012年，Constructionof soft porous crystal with silole derivative:strategy of framework design,multiple structural transformability and mechanofluorochromism.(J.Mater.Chem.,2012,22(10):4290-4298.)报导合成了以噻咯为母体结构的力致变色荧光材料Silole-CN；Piezofluorochromism of an Aggregation-Induced EmissionCompound Derived from Tetraphenylethylene(Chem-Asian.J.,2011,6(3):808-811.)和Benzothiazolium-functionalized tetra-phenylethene:an AIE luminogen withtunable solid-state emission.(Chem.Commun.,2012,48(69):8637-8639.)所报导的研究结果在发展四苯基乙烯类力致荧光变色材料方面做出了突出的贡献；此外，Twisted D-π-A solid emitters:efficient emission and high contrast mechanochromism(Chem.Commun.,2013,49(38):4009-4011.)Modularity Analysis of Tunable Solid-State Emission Based on a Twisted Conjugated Molecule Containing 9,9’-Bianthracene Group(Adv.Mater.,2013,25(42):6112-6116)也先后报导了一系列类四苯基乙烯的构象扭曲的力致变色分子。这些分子的共同特征是在外力的作用下，扭曲的分子构象相对平面化，分子共轭程度增加，分子的荧光发射发生明显红移。但是到目前为止，力致变色荧光材料的形成机理并没有统一的理论，力致变色材料的发展还远远落后于其他的一些刺激响应变色材料，如光致变色材料和电致变色材料。主要的问题集中在力致变色材料的种类较少，变色机理不太清楚，实际应用很难实现等。因此，从分子设计角度出发，基于不同的力致变色机理，优化分子结构，设计合成新型的力致变色AIE材料，以实现丰富力致变色AIE材料种类的目的具有重要的科学意义。
发明内容
本发明的目的是提供一类新型力致变色材料。
为此，本发明首先提供一类力致变色材料，是具有通式I结构的化合物：
所述的R1和R2各自独立地选自氢、C1-10烷基、C1-10烷氧基、C3-10环烷基、苯基、取代苯基、萘基、芘基、蒽基、菲基和醌基；
所述的取代苯基是由下述基团任意取代的苯基：C1-6烷基、C1-6烷氧基、硝基、卤素、氨基、苯胺基或二苯胺基。
另一方面，本发明也提供所述力致变色材料的制备方法，包括以下步骤：
(1)式i的化合物与式ii的化合物按照摩尔比1:1在路易斯酸催化条件下，于250-300℃回流反应24-36h，制备式iii的化合物；
其中，R3和R4各自独立地选自H、Br或I；
优选R4＝I，最优选R4＝I且R3是Br或H；
所述的路易斯酸选自AlCl3、ZnCl2或FeCl3。
(2)式iii的化合物依次与式iv和式v的化合物按照摩尔比1:1:1在碱性条件下、由Pd催化剂催化反应制备式vi的化合物；
所述的Pd催化剂是Pd(PPh3)4；
所述的碱性条件通过向反应体系中加入K2CO3、Cs2CO3、Na2CO3或NaHCO3构建；
所述的反应在有机溶剂的水溶液中进行，有机溶剂选自THF、甲苯或二甲苯；
所述的反应在氮气保护条件下进行；
(3)式vi的化合物与BF3.Et2O、Et3N按照摩尔比1:1在室温条件下反应2-4h制备通式I的化合物；
其中，所述的反应在有机溶剂中进行，有机溶剂选自CH2Cl2、CHCl3、CCl4、CS2、Et2O或THF。
本发明的具有力致变色材料具有以下有益效果：本发明的发光材料具有研磨变色特性，从610nm红移到了653nm，在研磨-熏蒸和研磨-加热过程中，由于分子在晶态和无定型之间变化，导致发光颜色可逆转变；鉴于该类材料的良好的力致变色性质，可以对聚合物进行掺杂，检测聚合物材料在使用过程中的损伤和老化。
附图说明
图1是化合物B1的合成路线图；
图2是化合物B1研磨前后固体紫外吸收谱图；
图3为化合物B1研磨前后荧光光谱图，研钵研磨2-3min，以420nm为激发波长；
图4为化合物B1研磨熏蒸荧光最大发射峰的循环图，研钵研磨2-3min，以CH2Cl2作为熏蒸溶剂，室温下熏蒸15min，420nm为激发波长；
图5为化合物B1的XRD谱图，CH2Cl2作为熏蒸溶剂，室温下熏蒸15min测试；
图6为化合物B1的在不同溶剂中的紫外谱图，分别以甲苯、氯仿、THF、DMF和乙腈为溶剂，浓度为5×10-5M；
图7为化合物B1的在不同溶剂中的荧光谱图，分别以甲苯、氯仿、THF、DMF和乙腈为溶剂，浓度为5×10-5M，420nm为激发波长。
具体实施方式
本发明提供了一类具有良好的力致变色性质的新型材料，具有通式结构I：
具体实施方式中，所述的R1和R2各自独立地选自氢、C1-6烷基、C1-6烷氧基、C3-6环烷基、苯基和取代苯基。更为具体地描述，所述的R1和R2各自独立地选自氢、C1-4烷基、C3-6环烷基、苯基，以及由C1-6烷基、卤素、氨基、苯胺基或二苯胺基任意取代的苯基。尤其优选地，所述的R1和R2各自独立地选自氢、C1-4烷基、苯基，以及由甲基、乙基、Cl、Br、-NH2、PhNH-、(Ph)2N-任意取代的苯基。其中Ph-代表苯基。
进一步的具体实施方式中，所述的R1和R2中，至少有一个取代基是以苯基为基础的基团，即苯基或取代苯基。这些取代苯基选自由甲基、乙基、Cl、Br、-NH2、PhNH-、(Ph)2N-任意取代的苯基，其中又尤以对位单取代的苯基为优选。
作为本发明最优选的实施方式中，所述的力致变色材料是化合物B1或化合物B2：
下述非限制性实施例用于对本发明的技术特征及效果作进一步的说明，不应当理解为对本发明任意形式的限定。
实施例1
化合物B1的合成：化合物B1的合成路线如附图1所示。
1)合成化合物1：将30mmol的4-溴吡啶甲醛和15mmol的吲哚酮放入反应瓶中，加入100ml的干燥的甲苯，加热回流10h，然后将此反应体系冷却，旋干溶剂，剩余物硅胶柱层析(石油醚：乙酸乙酯为5：1)得淡黄色粗产品，在石油醚乙酸乙酯的混合溶剂中重结晶得淡黄色白色固体，产率54％。
2)合成化合物2：将20mmol化合物1加到反应瓶中，加入四氢呋喃100ml，按照化合物1的摩尔量加入1.2当量的三苯胺的硼酸酯及催化剂1,1'-双(二苯基膦)二茂铁二氯化镍(Ni(dpppf)Cl2)，氮气气氛中，加热回流反应过夜。然后将此反应体系冷却，旋干溶剂，剩余物硅胶柱层析得到红色固体，产品用石油醚乙酸乙酯的混合溶剂重结晶得化合物2，为橙红色固体，产率81％。
3)合成化合物B1：将10mmol化合物2放入250ml的反应瓶中，加入CH2Cl260mL，并按照化合物2的摩尔投量加入1当量的Et2N，控温在0℃，将10mmol(1equiv)BF3·Et2O用注射器打入。反应混合物升到室温反应2h，在室温下自然升温反应过夜。旋干溶剂，剩余物硅胶柱层析得到粗产品用丙酮重结晶得化合物B1，产率75％。目标产物为黄绿色固体，可溶于普通有机溶剂，包括THF、二氯甲烷、氯仿和DMSO、DMF。
对所获得的化合物B1通过1H NMR、13C NMR、质谱检测，其结构数据为：1H NMR(400MHz,CDCl3,ppm)δ8.84(d,J＝1.5Hz,1H),8.13(dd,J＝8.5,2.1Hz,1H),7.92(d,J＝6.9Hz,1H),7.75(d,J＝7.1Hz,1H),7.60(ddd,J＝15.0,10.4,6.8Hz,2H),7.48(dd,J＝16.4,8.6Hz,3H),7.32(t,J＝7.9Hz,4H),7.22-7.04(m,8H),6.36(s,1H).13C NMR(100MHz,CDCl3)δ149.32,147.86,146.97,139.87,139.08,136.21,134.83,132.35,131.33,129.56,127.41,127.10,125.27,124.31,124.02,122.70,120.93,92.90.MALDI-TOF(m/z),calculated for C32H22BF2N3O[M]+513.18；found:513.12.
实施例2
(1)我们对化合物B1研磨前后的固体紫外进行测试，化合物B1研磨前后固体紫外谱图，如附图2所示，从图中我们可以看出化合物B1研磨前后固体紫外变化不大。通过对化合物B1研磨前后的固体荧光进行测试并计算得到化合物B1研磨前后固体荧光量子效率由1.9变为1.8。
(2)为检测本发明发光材料的研磨变色特性，将化合物B1放入研钵，研磨2-3min，以420nm为激发波长进行固体荧光光谱检测，结果如附图3所示。从图中可以看出：研磨之后，化合物B1的最大吸收峰从610nm红移到了653nm，相应的颜色由橙红色变为深红色。
(3)本试验测试了研磨及CH2Cl2熏蒸前后化合物B1的荧光最大发射峰循环特征。
将化合物B1放入研钵，研磨2-3min，以420nm为激发波长进行固体荧光光谱检测；以CH2Cl2作为熏蒸溶剂，室温下熏蒸15min以420nm为激发波长进行固体荧光光谱测试，结果如附图4所示。荧光最大发射峰循环图表明化合物B1在研磨和熏蒸后荧光最大发射峰有很好的重复性，这是因为分子在多次研磨和熏蒸后化合物B1在晶态和无定型态之间可逆转变。
(4)本试验测试了研磨及CH2Cl2熏蒸前后化合物B1的XRD峰特征。
我们利用CH2Cl2作为熏蒸溶剂，室温下熏蒸15min测试，研磨后固体由晶态转变为无定形态，XRD检测结果如附图5，其中标记为“合成的”是指未研磨或熏蒸之前的原始样品。从附图5中不难看出研磨后样品的XRD峰减少变弱，熏蒸后峰型及强度又变为原来的峰型和强度。说明在研磨-熏蒸过程中，由于分子在晶态和无定型之间变化，导致发光颜色可逆转变。
(5)本试验测试了在不同溶剂中化合物B1的紫外吸收特征。
分别以甲苯、氯仿、THF、DMF和乙腈为溶剂，配制浓度为5×10-5M的化合物B1的溶液，分别测定它们的紫外吸收谱图，结果如附图6所示。可以看出在不同溶剂中，化合物B1的最大吸收值随着溶剂极性的增加蓝移。
(6)本试验测试了在不同溶剂中化合物B1的荧光发射特征。
实验过程中我们以420nm为激发波长，溶液浓度定为5×10-5M，在常见溶剂甲苯、氯仿、THF、DMF、乙腈溶剂中的荧光发射光谱图。结果如附图7所示。通过谱图分析我们发现在不同溶剂中最大吸收随着溶剂极性的增加出现红移，且在大极性溶剂中如DMF或乙腈中出现荧光淬灭。

Claims (6)

1.一类力致变色材料，是具有通式I结构的化合物：
所述的R1和R2各自独立地选自氢、C1-10烷基、C1-10烷氧基、C3-10环烷基、苯基、取代苯基、萘基、芘基、蒽基、菲基和醌基；
所述的取代苯基是由下述基团任意取代的苯基：C1-6烷基、C1-6烷氧基、硝基、卤素、氨基、苯胺基或二苯胺基。
2.根据权利要求1所述的力致变色材料，其特征在于，所述的R1和R2各自独立地选自氢、C1-6烷基、C1-6烷氧基、C3-6环烷基、苯基和取代苯基。
3.根据权利要求2所述的力致变色材料，其特征在于，所述的R1和R2各自独立地选自氢、C1-4烷基、C3-6环烷基、苯基，以及由C1-6烷基、卤素、氨基、苯胺基或二苯胺基任意取代的苯基。
4.根据权利要求3所述的力致变色材料，其特征在于，所述的R1和R2各自独立地选自氢、C1-4烷基、苯基，以及由甲基、乙基、Cl、Br、-NH2、PhNH-、(Ph)2N-任意取代的苯基。
5.根据权利要求1所述的力致变色材料，是化合物B1或化合物B2：
6.权利要求1所述的力致变色材料的制备方法，包括以下步骤：
(1)式i的化合物与式ii的化合物按照摩尔比1:1在路易斯酸催化条件下，于250-300℃回流反应24-36h，制备式iii的化合物；
其中，R3和R4各自独立地选自H、Br或I；
所述的路易斯酸选自AlCl3、ZnCl2或FeCl3；
(2)式iii的化合物依次与式iv和式v的化合物按照摩尔比1:1:1在碱性条件下、由Pd催化剂催化反应制备式vi的化合物；
所述的Pd催化剂是Pd(PPh3)4；
所述的碱性条件通过向反应体系中加入K2CO3、Cs2CO3、Na2CO3或NaHCO3构建；
所述的反应在有机溶剂的水溶液中进行，有机溶剂选自THF、甲苯或二甲苯；
所述的反应在氮气保护条件下进行；
(3)式vi的化合物与BF3.Et2O、Et3N在室温条件下反应2-4h制备通式I的化合物；
其中，所述的反应在有机溶剂中进行，有机溶剂选自CH2Cl2、CHCl3、CCl4、CS2、Et2O或THF。
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