CN105567217A - 一种多刺激-响应有机小分子发光材料及制备与应用 - Google Patents
一种多刺激-响应有机小分子发光材料及制备与应用 Download PDFInfo
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Abstract
本发明属于智能材料技术领域,公开了一种多刺激-响应有机小分子发光材料及制备与应用。本发明利用吩噻嗪衍生物的双荧光特性,设计合成一系列发光材料,通过外界刺激作用来调节两种构象的相互转化,为刺激-响应发光材料提供一个简单可行有效的设计策略。本发明的制备方法以吩噻嗪作为主要反应原料,通过一系列简单的反应,得到各种目标产物。所得产物分子量确定,结构单一,且具有较低的玻璃化转变温度,大大提高了其刺激-响应的灵敏性;本发明所得材料的刺激-响应原理是两个不同构象之间的转换,不是分子间的作用力和堆积方式的影响,使得其具有多刺激-相应的特点,可应用于力、温度、酸碱度等传感器中。
Description
技术领域
本发明属于智能材料技术领域,具体涉及一种多刺激-响应有机小分子发光材料及制备与应用。
背景技术
“智能材料”是一种能感知外部刺激(比如外力,温度,湿度,酸碱度,电场,磁场等),能够判断并适当处理且本身可执行的新型功能材料。因此,智能材料又称为刺激-响应材料。智能材料是继天然材料、合成高分子材料、人工设计材料之后的第四代材料,是现代高技术新材料发展的重要方向之一,将支撑未来高技术的发展,使传统意义下的功能材料和结构材料之间的界线逐渐消失,实现结构功能化、功能多样化。因此对智能材料的研发具有十分重要的意义。
刺激-响应发光材料是一类对外界刺激产生发光颜色变化响应的新型智能材料。固态下的发光材料的荧光特性与其分子堆积排列方式、构象、分子间的相互作用有着紧密的联系。因此通过摩擦、机械研磨、粉碎、压延等外力以及温度等作用改变分子堆积和构象以及分子间的相互作用(如分子间氢键、偶极矩、π-π作用力),实现晶态与无定形态或者不同晶型之间的相互转化,就能够导致其发光颜色发生变化。根据这一特性,刺激响应发光材料在传感器、信息存储设备、商标防伪等领域有着重要的潜在应用。近年来,受到了人们极大的关注。
但是目前关于刺激-响应发光材料的报道依然非常稀少。从总体上看,各类已报道的刺激-响应发光化合物之间基本上没有多大的关联性,基本上属孤立事件,尚没有规律可以用于该类发光化合物的设计。基于此,为刺激-响应发光材料提供一个简单可行有效的设计策略,研究开发新型刺激-响应材料具有十分重要的学术研究意义与巨大的经济价值。
吩噻嗪衍生物存在两种不同的杂化方式,因此存在两种较稳定的构象,从而体现出双荧光特性。由于两种构象的基态能量相近,理论上,两种构象可以通过外界的刺激作用相互转化。这使得吩噻嗪衍生物发光材料具有刺激-响应特性成为可能。
发明内容
基于以上现有技术,本发明的首要目的在于提供一种多刺激-响应有机小分子发光材料。该多刺激-响应有机小分子发光材料基于吩噻嗪衍生物的双荧光特性,为刺激-响应发光材料提供一个简单可行有效的设计策略。
本发明的另一目的在于提供上述多刺激-响应有机小分子发光材料的制备方法。
本发明的再一目的在于提供上述多刺激-响应有机小分子发光材料在力、温度、酸碱度等传感器中的应用。
本发明目的通过以下技术方案实现:
一种多刺激-响应有机小分子发光材料,所述材料具有如下P1n或P2n所示的化学结构式:
其中,Ar表示以下(1)~(7)中任意一种类型的芳香基团:
优选地,所述多刺激-响应有机小分子发光材料具有如下P1~P14中任一项所示的结构式:
上述多刺激-响应有机小分子发光材料的制备方法,包括以下制备步骤:
(1)制备以下1~6任一项所述的中间体或使用4-溴二苯甲酮,
(2)将步骤(1)的中间体或4-溴二苯甲酮与吩噻嗪或N-对苯硼酸基吩噻嗪反应,得到所述多刺激-响应有机小分子发光材料。
上述多刺激-响应有机小分子发光材料在力、温度、酸碱度等传感器中的应用。
所述应用基于的原理是:本发明所得多刺激-响应有机小分子发光材料所含吩噻嗪衍生物结构具有两种不同的杂化方式,因此存在两种较稳定的构象,从而体现出双荧光特性;分子在力、温度、酸碱度等外在刺激作用下会发生两种构象之间的相互转化,从而发光颜色发生变化,可应用于力、温度、酸碱度等传感器。
本发明的制备方法及所得到的产物具有如下优点及有益效果:
(1)本发明的多刺激-响应有机小分子发光材料基于吩噻嗪衍生物双荧光的特性,其结构单一,分子量确定,合成方法简单,便于提纯,多次合成再现性好;
(2)本发明的多刺激-响应有机小分子发光材料基于吩噻嗪衍生物双荧光的特性,具有较低的玻璃化转变温度,大大提高了其刺激-响应的灵敏性;
(3)本发明的多刺激-响应有机小分子发光材料具有聚集诱导增强发光(AIE)特性;
(4)本发明的多刺激-响应有机小分子发光材料的变色原理是两个不同构象之间的转换,不是分子间的作用力和堆积方式的影响,使得其具有多刺激-响应的特点;
(5)本发明的多刺激-响应有机小分子发光材料,将吩噻嗪衍生物双荧光的特性应用到刺激-响应发光材料中,通过外界的作用,调节构象之间的转换,为刺激-响应发光材料提供一个简单可行有效的设计策略。
附图说明
图1是P1和P11在四氢呋喃溶液中的吸收光谱图;
图2是P1和P11粉末的发光光谱图;
图3是P1(左)和P11(右)在不同含水量的水和四氢呋喃溶液中的发光光谱图;
图4~6分别为P1(左)和P11(右)在含水量为99%的水和四氢呋喃的溶液对鼓氩气、搅拌以及研磨力的刺激-响应结果图。
具体实施方式
下面结合实施例及附图对本发明作进一步详细的描述,但本发明的实施方式不限于此。
实施例1
(1)准备合成原料4-溴二苯甲酮;
(2)多刺激-响应有机小分子发光材料P1的制备,具体合成路线如下式所示:
具体实施步骤为:
在氮气保护下,向三口烧瓶中加入100ml甲苯,1g4-溴二苯甲酮(3.85mmol),0.92g的吩噻嗪(4.62mmol,1.2equ),在搅拌下加入0.58g叔丁基醇钠,再加入38.5mgPd(OAc)2(醋酸钯),三特丁基膦,90℃下反应过夜。降温,用二氯甲烷萃取有机相,旋干,过柱。得黄色色固体产物1.17g,产率80%。分子式:C25H17NOS;M/Z=379.10理论值:379.10(100.0%),380.11(27.0%),381.10(4.5%),381.11(2.7%),382.10(1.2%);元素分析:C,79.13;H,4.52;N,3.69;O,4.22;S,8.45。
实施例2
(1)准备合成原料4-溴二苯甲酮;
(2)多刺激-响应有机小分子发光材料P2的制备,具体合成路线如下式所示:
具体实施步骤为:
在氮气保护下,向三口烧瓶中加入100ml甲苯,1g4-溴二苯甲酮(3.85mmol),1.5g中间体7(N-对苯硼酸基吩噻嗪),在搅拌下加入2M碳酸钾水溶液25mL和25mL乙醇,再加入200mg四(三苯膦)钯{Pd(PPh3)4},90℃下反应过夜。反应完降温,用二氯甲烷萃取有机相,旋干,过柱。得黄色固体产物1.44g,产率84%。分子式:C31H21NOS;M/Z=379.10理论值:517.08(100.0%),518.09(33.5%),519.09(5.4%),519.08(4.5%),520.08(1.5%);元素分析:C,71.95;H,4.09;N,2.71;O,3.09;P,11.97;S,6.19。
所述中间体7的合成路线如下式所示:
具体实施步骤为:
在氮气保护下,于100ml三口烧瓶中加入吩噻嗪3.98g(20mmol)和4.40g对溴苯硼酸(22mmol,1.1equ)以及1.27g碘化亚铜,加入溶剂氮氮二甲基甲酰胺100ml,在加热至200℃反应24小时,反应完成,降温,用二氯甲烷萃取,过硅胶柱得到4.47g产物,产率70%,C18H14BNO2SM/S=319.08。理论值:319.08(100.0%),318.09(24.8%),320.09(9.7%),320.09(9.7%),319.09(4.8%),321.08(4.5%),321.09(1.8%),320.08(1.1%);元素分析:C,67.73;H,4.42;B,3.39;N,4.39;O,10.02;S,10.04。
实施例3
(1)制备中间体1,具体合成路线如下式所示:
具体实施步骤为:
在氮气气氛下,于100ml两口烧瓶中加入2-溴吡啶1.26g(8mmol),用30ml四氢呋喃溶解;于50ml茄形瓶中加入2.21g对溴苯甲醛(12mmol,1.5equ),用20ml四氢呋喃溶解。将2-溴吡啶四氢呋喃溶液用液氮把体系降温到-110℃,通氩气,保温30分钟后,缓慢滴加3.2ml的2.5M正丁基锂(8mmol,1equ)。滴完后,反应一小时。将对溴苯甲醛四氢呋喃注入到反应体系后,于室温搅拌反应三小时。反应完成后,将四氢呋喃旋蒸干,用二氯甲烷和水萃取三次,将二氯甲烷旋蒸干后得到黄色油状物。将黄色油状物用50ml二氯甲烷溶解于100ml单口瓶中,加入5.17g氯铬酸吡啶(PCC,24mmol,3equ),在室温下搅拌氧化四小时,反应完成,加入1.5倍氯铬酸吡啶重量的硅胶,减压蒸馏除掉二氯甲烷,硅胶柱提纯,得到结构式1的中间体1.57g,产率75%,C12H8BrNOM/Z=260.95。m/s:260.98(100.0%),262.98(97.3%),261.98(13.0%),263.98(12.6%);元素分析:C,54.99;H,3.08;Br,30.49;N,5.34;O,6.10。
(2)多刺激-响应有机小分子发光材料P3的制备,具体合成路线如下式所示:
具体实施步骤为:
将实施例1中的4-溴二苯甲酮换成等当量的中间体1,其他原料和步骤均同于实施例1,得黄色固体产物1.20g,产率82.1%。分子式:C24H16N2OS;M/Z=380.10理论值:380.10(100.0%),381.10(26.0%),382.09(4.5%),382.11(2.7%),383.10(1.2%);元素分析:C,75.77;H,4.24;N,7.36;O,4.21;S,8.43。
实施例4
(1)制备中间体1,与实施例3相同;
(2)多刺激-响应有机小分子发光材料P4的制备,具体合成路线如下式所示:
具体实施步骤为:
将实施例2中的4-溴二苯甲酮换成等当量的中间体1,其他原料和步骤均同于实施例2,得黄色固体产物1.50g,产率87.5%。分子式:C30H20N2OS;M/Z=456.13理论值:456.13(100.0%),457.13(32.4%),458.13(4.5%),458.14(2.7%),458.14(2.4%),459.13(1.5%);元素分析:C,78.92;H,4.42;N,6.14;O,3.50;S,7.02。
实施例5
(1)制备中间体2,具体合成路线如下式所示:
具体实施步骤为:
实施例3中的2-溴吡啶换成等当量的3-溴吡啶,其他原料和步骤均同于实施例3,得结构式2的中间体1.50g,产率72%。C12H8BrNOM/Z=260.95。m/z:260.98(100.0%),262.98(97.3%),261.98(13.0%),263.98(12.6%);元素分析:C,54.99;H,3.08;Br,30.49;N,5.34;O,6.10。
(2)多刺激-响应有机小分子发光材料P5的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例1中的4-溴二苯甲酮换成等当量的中间体2,其他原料和步骤均同于实施例1,得黄色固体产物1.00g,产率68.42%。分子式:C24H16N2OS;M/Z=380.10理论值:380.10(100.0%),381.10(26.0%),382.09(4.5%),382.11(2.7%),383.10(1.2%);元素分析:C,75.77;H,4.24;N,7.36;O,4.21;S,8.43。
实施例6
(1)制备中间体2,与实施例5相同;
(2)多刺激-响应有机小分子发光材料P6的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例2中的4-溴二苯甲酮换成等当量的中间体2,其他原料和步骤均同于实施例2,得黄色固体产物1.40g,产率82.7%。分子式:C30H20N2OS;M/Z=456.13理论值:456.13(100.0%),457.13(32.4%),458.13(4.5%),458.14(2.7%),458.14(2.4%),459.13(1.5%);元素分析:C,78.92;H,4.42;N,6.14;O,3.50;S,7.02。
实施例7
(1)制备中间体3,合成路线如下式所示:
具体实施步骤为:
在氮气气氛下,于100ml两口烧瓶中加入对溴碘苯2.25g(8mmol),用30ml四氢呋喃溶解;于50ml茄形瓶中加入2.21g4-吡啶苯甲醛(12mmol,1.5equ),用20ml四氢呋喃溶解。将对溴碘苯的四氢呋喃溶液用液氮把体系降温到-110℃,通氩气,保温30分钟后,缓慢滴加3.2ml的2.5M正丁基锂(8mmol,1equ)。滴完后,反应一小时。将4-吡啶苯甲醛四氢呋喃注入到反应体系后,于室温搅拌反应三小时。反应完成后,将四氢呋喃旋蒸干,用二氯甲烷和水萃取三次,将二氯甲烷旋蒸干后得到黄色油状物。将黄色油状物用50ml二氯甲烷溶解于100ml单口瓶中,加入5.17g氯铬酸吡啶(24mmol,3equ),在室温下搅拌氧化四小时,反应完成,加入1.5倍氯铬酸吡啶重量的硅胶,减压蒸馏除掉二氯甲烷,硅胶柱提纯,得到结构式3的中间体1.58g,产率76%,C12H8BrNOM/Z=260.98。m/z:260.98(100.0%),262.98(97.3%),261.98(13.0%),263.98(12.6%);元素分析:C,54.99;H,3.08;Br,30.49;N,5.34;O,6.10。
(2)多刺激-响应有机小分子发光材料P7的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例1中的4-溴二苯甲酮换成等当量的中间体3,其他原料和步骤均同于实施例1,得黄色固体产物1.10g,产率75.26%。分子式:C24H16N2OS;M/Z=380.10理论值:380.10(100.0%),381.10(26.0%),382.09(4.5%),382.11(2.7%),383.10(1.2%);元素分析:C,75.77;H,4.24;N,7.36;O,4.21;S,8.43。
实施例8
(1)制备中间体3,与实施例7相同;
(2)多刺激-响应有机小分子发光材料P8的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例2中的4-溴二苯甲酮换成等当量的中间体3,其他原料和步骤均同于实施例2,得黄色固体产物1.25g,产率73.8%。分子式:C30H20N2OS;M/Z=456.13理论值:456.13(100.0%),457.13(32.4%),458.13(4.5%),458.14(2.7%),458.14(2.4%),459.13(1.5%);元素分析:C,78.92;H,4.42;N,6.14;O,3.50;S,7.02。
实施例9
(1)制备中间体4,合成路线如下式所示:
具体实施步骤为:
实施例3中的2-溴吡啶换成等当量的2-溴嘧啶,其他原料和步骤均同于实施例3,得结构式4的中间体体产物1.50g,产率72%,C12H7BrN2OM/Z=261.97。理论值:261.97(100.0%),263.97(97.3%),262.98(11.9%),264.98(11.6%);元素分析:261.97(100.0%),263.97(97.3%),262.98(11.9%),264.98(11.6%)。
(2)多刺激-响应有机小分子发光材料P9的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例1中的4-溴二苯甲酮换成等当量的中间体4,其他原料和步骤均同于实施例1,得黄色固体产物1.30g,产率88.9%。分子式:C23H15N3OS;M/Z=381.09理论值:381.09(100.0%),382.10(24.9%),383.09(4.5%),383.10(2.7%),384.09(1.1%),382.09(1.1%);元素分析:CC,72.42;H,3.96;N,11.02;O,4.19;S,8.40。
实施例10
(1)制备中间体4,与实施例9相同;
(2)多刺激-响应有机小分子发光材料P10的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例2中的4-溴二苯甲酮换成等当量的中间体4,其他原料和步骤均同于实施例2,得黄色固体产物1.20g,产率70.8%。分子式:C29H19N3OS;M/Z=457.12理论值:457.12(100.0%),458.13(31.4%),459.12(4.5%),459.13(2.7%),459.13(2.0%),460.12(1.4%),458.12(1.1%);元素分析:C,76.13;H,4.19;N,9.18;O,3.50;S,7.01。
实施例11
(1)制备中间体5,合成路线如下式所示:
具体实施步骤为:
实施例3中的2-溴吡啶换成等当量的5-溴嘧啶,其他原料和步骤均同于实施例3,得结构式5的中间体产物1.67g,产率80%,C12H7BrN2OM/Z=261.97。理论值:261.97(100.0%),263.97(97.3%),262.98(11.9%),264.98(11.6%);元素分析:C,50.22;H,2.68;Br,30.37;N,10.65;O,6.08。
(2)多刺激-响应有机小分子发光材料P11的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例1中的4-溴二苯甲酮换成等当量的中间体5,其他原料和步骤均同于实施例1,得黄色固体产物1.10g,产率75.2%。分子式:C23H15N3OS;M/Z=381.09理论值:381.09(100.0%),382.10(24.9%),383.09(4.5%),383.10(2.7%),384.09(1.1%),382.09(1.1%);元素分析:C,72.42;H,3.96;N,11.02;O,4.19;S,8.40。
实施例12
(1)制备中间体5,与实施例11相同;
(2)多刺激-响应有机小分子发光材料P12的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例2中的4-溴二苯甲酮换成等当量的中间体5,其他原料和步骤均同于实施例2,得黄色固体产物1.25g,产率73.8%。分子式:C29H19N3OS;M/Z=457.12理论值:457.12(100.0%),458.13(31.4%),459.12(4.5%),459.13(2.7%),459.13(2.0%),460.12(1.4%),458.12(1.1%);元素分析:C,76.13;H,4.19;N,9.18;O,3.50;S,7.01。
实施例13
(1)制备中间体6,合成路线如下式所示:
具体实施步骤为:
实施例3中的2-溴吡啶换成等当量的2-溴-4,6-二苯基-1,3,5-三嗪,其他原料和步骤均同于实施例3,得结构式6的中间体体产物2.00g,产率80%,C15H10BrN3M/Z=311.01。理论值:11.01(100.0%),313.00(97.3%),312.01(16.2%),314.01(15.8%),315.01(1.2%),312.00(1.1%),314.00(1.1%),313.01(1.1%);元素分析:C,57.71;H,3.23;Br,25.60;N,13.46。
(2)多刺激-响应有机小分子发光材料P13的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例1中的4-溴二苯甲酮换成等当量的中间体6,其他原料和步骤均同于实施例1,得黄色固体产物1.6g,产率78.9%。分子式:C34H22N4OS;M/Z=534.15理论值:34.15(100.0%),535.15(36.8%),536.15(4.5%),536.16(3.9%),536.16(2.7%),537.15(1.7%),535.15(1.5%);元素分析:C,76.38;H,4.15;N,10.48;O,2.99;S,6.00。
实施例14
(1)制备中间体6,与实施例11相同;
(2)多刺激-响应有机小分子发光材料P14的制备,具体合成路线如下式所示:
具体实施步骤为:
实施例2中的4-溴二苯甲酮换成等当量的中间体6,其他原料和步骤均同于实施例2,得黄色固体产物1.41g,产率60%。分子式:C40H26N4OS;M/Z=610.18理论值:610.18(100.0%),611.19(43.3%),612.19(9.1%),612.18(4.5%),613.18(2.0%),611.18(1.5%),613.19(1.1%);元素分析:C,78.67;H,4.29;N,9.17;O,2.62;S,5.25。
本发明所得多刺激-响应有机小分子发光材料性能及多刺激-响应效果测试:
选取P1和P11这两种产物作为测试对象:
P1和P11在四氢呋喃溶液中的吸收光谱图如图1所示;
P1和P11粉末的发光光谱图如图2所示,由图2可以看出本发明所得产物具有吩噻嗪衍生物双荧光的特性。
P1(左)和P11(右)在不同含水量的水和四氢呋喃溶液中的发光光谱如图3所示,由图3可以看出本发明的多刺激-响应有机小分子发光材料具有聚集诱导增强发光(AIE)特性。
P1(左)和P11(右)在含水量为99%的水和四氢呋喃的溶液对鼓氩气、搅拌以及研磨力的刺激-响应分别如图4、图5和图6所示。由图4~6可以看出,本发明的有机小分子发光材料具有良好的多刺激-响应特性。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其它的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (4)
1.一种多刺激-响应有机小分子发光材料,其特征在于所述材料具有如下P1n或P2n所示的化学结构式:
其中,Ar表示以下(1)~(7)中任意一种类型的芳香基团:
2.根据权利要求1所述的一种多刺激-响应有机小分子发光材料,其特征在于:所述材料具有如下P1~P14中任一项所示的结构式:
3.权利要求1或2所述的一种多刺激-响应有机小分子发光材料的制备方法,其特征在于包括以下制备步骤:
(1)制备以下1~6任一项所述的中间体或使用4-溴二苯甲酮,
(2)将步骤(1)的中间体或4-溴二苯甲酮与吩噻嗪或N-对苯硼酸基吩噻嗪反应,得到所述多刺激-响应有机小分子发光材料。
4.权利要求1或2所述的多刺激-响应有机小分子发光材料在力、温度、酸碱度传感器中的应用。
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