CN117924290A - 一种滤纸基质的长寿命有机室温磷光材料的制备方法及应用 - Google Patents
一种滤纸基质的长寿命有机室温磷光材料的制备方法及应用 Download PDFInfo
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
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Abstract
本发明设计、合成一种低成本和长磷光寿命的有机室温磷光材料,提供一种制备路线简单,同时具有长发光寿命的一种滤纸基质有机室温磷光材料的新制备方法,本发明中制备的磷光分子的化学分子式为C42H26Br2N2O4S2,分子量为846.6080,分子结构为:
Description
技术领域
本发明涉及发光材料技术领域,具体是关于一种滤纸基质的长寿命有机室温磷光材料的制备方法及应用。
背景技术
有机室温磷光材料因为具有较大的斯托克斯位移、较长的衰减寿命以及长余辉等特点,在防伪材料、分子开关和生物成像等领域有着重要的应用价值。与传统的无机或金属有机磷光体系相比,纯有机室温磷光材料具有安全无毒、价格低廉和可加工性好等优势,有着广泛的应用前景。然而纯有机室温磷光材料非常稀缺,现有的制备过程繁琐复杂、合成条件苛刻,严重限制了磷光材料的大规模应用。因此,发展高效、长寿命的磷光材料以及探索其在前沿科技领域的应用价值十分必要。
在室温下想要实现高效纯有机磷光发射,主要难点在于如何有效地调控分子内/间的自旋-轨道耦合作用以促进单线态激子经系间窜跃成三线态激子,进而实现高效磷光发射纯有机RTP材料。然而,目前有机发光材料领域已有的方法大部分都需要精巧的分子设计和复杂的合成手段。滤纸具有分析方法简便,使用广泛,易于裁剪的优点,因而我们开发了合成方法简洁的滤纸基底的纯有机室温磷光材料的构建策略。
化合物中的重原子可以在掺入其中的染料受激发后通过外部重原子效应促进其系间窜越(ISC)过程,从而诱导其激发三重态的产生。与此同时,磷光分子渗入到滤纸纤维中并被嵌入进而实现刚性化,从而抑制了磷光体的非辐射跃迁过程。也就是说,染料激发三重态的产生和稳定都通过同一个聚合物基质实现了,从而诱导了其室温磷光。
结合以上分析,本发明设计、合成出的一种滤纸基质的长寿命有机室温磷光材料,可将其应用于印刷及防伪领域。该磷光材料具有制备路线简单、价格低廉、发光寿命长、制作成本低等特点,为有机室温磷光材料的进一步研究指出了一个方向。
发明内容
本发明的目的是针对上述存在问题,提供一种制备路线简单,同时具有长发光寿命的一种滤纸基质有机室温磷光材料的制备及其应用。
本发明的技术方案:
本发明设计、合成一种低成本和长磷光寿命的有机室温磷光材料,本发明中制备的磷光分子的化学分子式为C42H26Br2N2O4S2,分子量为846.6080,分子结构为:
制备步骤如下:
1)1-溴-2-((4-氟苯基)磺酰)苯:将2-溴-苯磺酰氯(2.0g,7.83mmol)和氟苯(2.2ml, 23.49mmol)放入三口烧瓶中,在氩气氛围下加入无水三氯化铁(2.54g,15.66mmol),室温反应2h后,用10mL1M HCl猝灭。混合物用二氯甲烷萃取三次,用水洗涤,用无水硫酸镁干燥。经过减压过滤,滤液经柱层析法纯化(二氯甲烷/石油醚,1/2,v/v),得到白色固体(1.79g,收率72.5%)。
反应式为:
2)5,11-双(4-(2-溴苯基)磺酰基)苯基)-5,11-二氢吲哚[3,2-b]咔唑:在氮气气氛保护下,将5,11-二氢吲哚并[3,2-b]咔唑(271.7mg,1.06mmol)加入三口瓶中,加入 DMF10mL搅拌使之溶解。加入叔丁醇钾(237.9mg,2.12mmol)搅拌10min后,加入1-溴-2-((4-氟苯基)磺酰)苯(1g,3.17mmol)。升温至100℃继续搅拌反应5h。反应完成后冷却至室温,将反应液倒入20mL水中进行沉淀,抽滤,水洗,得到淡黄色固体(440.5mg,产率49.1%)。1H NMR(400MHz,DMSO-d6)δ(ppm):8.46(d, J=1.8Hz,1H),8.44(d,J=1.7Hz,1H),8.42(d,J=4.4Hz,2H),8.39(s,1H),8.26 (d,J=8.7Hz,4H),8.07(d,J=8.6Hz,4H),7.94(d,J=7.9Hz,2H),7.81(t,J=7.6 Hz,3H),7.74-7.69(m,2H),7.54(d,J=8.2Hz,2H),7.46(t,J=7.7Hz,2H),7.30 (t,J=7.4Hz,2H).MS(ESI+)(m/z):[M+H]+calcd.for C42H27Br2N2O482 +:847.6155, found,847.6140.
反应式:
所述2-溴-苯磺酰氯、氟苯、无水三氯化铁的质量比为1∶1.13∶1.27
所述将1-溴-2-((4-氟苯基)磺酰)苯、5,11-二氢吲哚并[3,2-b]咔唑、t-BuOK质量比为1∶0.27∶0.24
滤纸基质的长寿命有机室温磷光材料的效果如下:
将加入化合物分子的滤纸烘干后,在紫外光激发下(例如365nm紫外光激发) 可以观察到长余辉现象,磷光寿命在室温条件下最高长达760ms。
本发明的优点是:该制备方法合成步骤简单、收率高、成本低,适于规模化生产,可以应用于制备防伪标志。
附图说明
图1为滤纸基质有机室温磷光材料的紫外吸收光谱图。
图2为滤纸基质有机室温磷光材料加碱前后的磷光光谱图。
图3为滤纸基质有机室温磷光材料的磷光寿命图。
具体实施方案
下面通过实施例具体的说明本发明,但本发明不受下述实施例的限定。
实施例:
本发明设计、合成一种低成本和长磷光寿命的有机室温磷光材料的制备方法及其应用,本发明中制备的磷光分子的化学分子式为C42H26Br2N2O4S2,分子量为846.6080,分子结构为:
制备步骤如下:
1)1-溴-2-((4-氟苯基)磺酰)苯:将2-溴-苯磺酰氯(2.0g,7.83mmol)和氟苯(2.2ml,23.49mmol)放入三口烧瓶中,在氩气氛围下加入无水三氯化铁(2.54g,15.66mmol),室温反应2h后,用10mL1M HCl猝灭。混合物用二氯甲烷萃取三次,用水洗涤,用无水硫酸镁干燥。经过减压过滤,滤液经柱层析法纯化(二氯甲烷/石油醚,1/2,v/v),得到白色固体(1.79g,收率72.5%)。
反应式为:
2)5,11-双(4-(2-溴苯基)磺酰基)苯基)-5,11-二氢吲哚[3,2-b]咔唑:在氮气气氛保护下,将5,11-二氢吲哚并[3,2-b]咔唑(271.7mg,1.06mmol)加入三口瓶中,加入 DMF10mL搅拌使之溶解。加入叔丁醇钾(237.9mg,2.12mmol)搅拌10min后,加入1-溴-2-((4-氟苯基)磺酰)苯(1g,3.17mmol)。升温至100℃继续搅拌反应5h。反应完成后冷却至室温,将反应液倒入20mL水中进行沉淀,抽滤,水洗,得到淡黄色固体(440.5mg,产率49.1%)。1H NMR(400MHz,DMSO-d6)δ(ppm):8.46(d, J=1.8Hz,1H),8.44(d,J=1.7Hz,1H),8.42(d,J=4.4Hz,2H),8.39(s,1H),8.26 (d,J=8.7Hz,4H),8.07(d,J=8.6Hz,4H),7.94(d,J=7.9Hz,2H),7.81(t,J=7.6 Hz,3H),7.74-7.69(m,2H),7.54(d,J=8.2Hz,2H),7.46(t,J=7.7Hz,2H),7.30 (t,J=7.4Hz,2H).MS(ESI+)(m/z):[M+H]+calcd.for C42H27Br2N2O482 +:847.6155, found,847.6140.
反应式:
3)滤纸基质的长寿命有机室温磷光材料的制备:将20mg 5,11-双(4-(2-溴苯基)磺酰基)苯基)-5,11-二氢吲哚[3,2-b]咔唑加入8ml DMF溶液中得到该化合物的饱和溶液,120℃加热10min充分溶解,滴到用叔丁醇钾浸湿的滤纸上,待滤纸烘干后,即可得到滤纸基质的长寿命有机室温磷光材料。
图1是滤纸基质有机室温磷光材料的紫外吸收光谱图,从图中可以看出,该材料在340nm处有较强的紫外吸收。
图2是滤纸基质有机室温磷光材料的磷光光谱图,图中纵坐标为磷光强度(a.u.),横坐标为波长(nm);可以看出,加碱后滤纸有较强的变化,在光致发光光谱测试下,既能发射出波长在423nm的荧光,也能发射出波长在500nm的磷光。
图3是滤纸基质有机室温磷光材料的磷光寿命图,图中表明该材料在紫外光激发下可以观察到长余辉现象,磷光寿命在室温条件下最高长达760ms。
Claims (5)
1.本发明设计、合成一种低成本和长磷光寿命的有机室温磷光材料,本发明中制备的磷光分子的化学分子式为C42H26Br2N2O4S2,分子量为846.6080,分子结构为:
制备步骤如下:
1)将2-溴-苯磺酰氯(2.0g,7.83mmol)和氟苯(2.2ml,23.49mmol)放入三口烧瓶中,在氩气氛围下加入无水三氯化铁(2.54g,15.66mmol),室温反应2h后,用10mL1M HCl猝灭。混合物用二氯甲烷萃取三次,用水洗涤,用无水硫酸镁干燥。经过减压过滤,滤液经柱层析法纯化(二氯甲烷/石油醚,1/2,v/v),得到白色固体(1.79g,收率72.5%)。
反应式为:
2)5,11-双(4-(2-溴苯基)磺酰基)苯基)-5,11-二氢吲哚[3,2-b]咔唑:在氮气气氛保护下,将5,11-二氢吲哚并[3,2-b]咔唑(271.7mg,1.06mmol)加入三口瓶中,加入DMF 10mL搅拌使之溶解。加入叔丁醇钾(237.9mg,2.12mmol)搅拌10min后,加入1-溴-2-((4-氟苯基)磺酰)苯(1g,3.17mmol)。升温至100℃继续搅拌反应5h。反应完成后冷却至室温,将反应液倒入20mL水中进行沉淀,抽滤,水洗,得到淡黄色固体(440.5mg,产率49.1%)。1H NMR(400MHz,DMSO-d6)δ(ppm):8.46(d,J=1.8Hz,1H),8.44(d,J=1.7Hz,1H),8.42(d,J=4.4Hz,2H),8.39(s,1H),8.26(d,J=8.7Hz,4H),8.07(d,J=8.6Hz,4H),7.94(d,J=7.9Hz,2H),7.81(t,J=7.6Hz,3H),7.74-7.69(m,2H),7.54(d,J=8.2Hz,2H),7.46(t,J=7.7Hz,2H),7.30(t,J=7.4Hz,2H).MS(ESI+)(m/z):[M+H]+calcd.for C42H27Br2N2O4S2 +:847.6155,found,847.6140.
反应式:
2.根据权利要求1所述,将2-溴-苯磺酰氯、氟苯的摩尔比为1∶3。
3.根据权利要求1所述,所述2-溴-苯磺酰氯、无水三氯化铁的摩尔比为1∶1.5。
4.根据权利要求1所述,所述1-溴-2-((4-氟苯基)磺酰)苯、5,11-二氢吲哚并[3,2-b]咔唑的摩尔比为1∶0.33。
5.根据权利要求1所述,所述1-溴-2-((4-氟苯基)磺酰)苯、t-BuOK的摩尔比为1∶0.67。
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