CN107459488B - 异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物及其制备方法 - Google Patents
异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物及其制备方法 Download PDFInfo
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Abstract
本发明公开了一种异长叶烷基并嘧啶‑2‑胺席夫碱类荧光化合物及其制备方法。该制备方法以乙醇为溶剂、乙酸为催化剂,天然可再生资源长叶烯的衍生物异长叶烷基并嘧啶‑2‑胺衍生物与2‑羟基‑1‑萘甲醛缩合,得到固体状异长叶烷基并嘧啶‑2‑胺席夫碱粗产物,将所得粗产物在无水乙醇中进行重结晶,得到异长叶烷基并嘧啶‑2‑胺席夫碱类化合物。本发明利用天然产物长叶烯衍生物异长叶烷基并嘧啶‑2‑胺为原料,制备了异长叶烷基并嘧啶‑2‑胺席夫碱类化合物;该类化合物在具有很好的固体荧光强度,在日光下表现为黄色,在紫外灯照射下可发出亮绿色或者亮黄色荧光,具有良好的荧光性能,可用作一类新型的有机小分子荧光染料。
Description
技术领域
本发明属精细有机合成技术领域,涉及异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物及其制备方法。
背景技术
有机小分子固体荧光材料在电致发光,光致发光,细胞荧光成像,显示器件等方面有着广泛的应用,因此,对于有机固体荧光材料的研究已经成为热点,尤其有机固体荧光材料在光电领域的优异表现受到人们的广泛关注。有机固体发光材料与无机发光材料相比具有很多优势,例如在可见光区域内有较高的摩尔消光系数、较大的Stokes位移、可修饰性强和种类繁多等优点,因此有机固体发光材料在许多领域都有重要的应用,比如有机发光二极管(OLEDs)、有机发光场效应晶体管(OLEFETs)、有机固体激光器等。
近年来出现了一些对于有机小分子荧光材料合成及其光学性能的研究,2007年,Yamaguchi课题组通过在联噻吩骨架上修饰含硼的大位阻基团得到了一系列具有强固体荧光的化合物。在分子结构中,联噻吩为供电子基团,大位阻基团Mes2B作为吸电子基团,分子内形成推拉电子结构,同时大位阻Mes2B基团还可以阻止分子间的电子相互作用,导致这类化合物不仅在溶液中有很强的荧光,并且在固体状态下也有很强的荧光。
2010年,Park课题组报道一个氰基取代的二苯乙烯衍生物,它在固体状态时有两种稳定的堆积模式,B(blue)模式和G(green)模式,这两种模式可以通过研磨、加热或溶剂蒸汽处理等多种刺激而相互转化。分子有两个局部偶极子,这两种堆积模式是局部偶极子偶合方式不同的结果。另外,该分子是一个可以滑动的平面分子,分子间存在多重氢键使得两种堆积模式可以很容易地相互转化而又能稳定存在。在这两种堆积模式中,它们的π-π重叠差异很大,从而导致它们的光学性质发生很大变化。最后,作者把荧光分子掺杂到PMMA中,成功制备了一个可以对压力、热和溶剂蒸汽快速响应的薄膜,成为第一个可多途径写入与擦除的荧光记录器件,能够灵敏实时地对外界的刺激进行响应的智能材料必将会在以后的科研和应用中占据重要地位。超分子化学的发展为设计新型的荧光功能材料提供了更加广阔的空间。
发明内容
发明目的:针对现有技术中存在的不足,本发明的目的在于提供一种异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物,满足使用需求。本发明的另一目的是提供一种上述异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物的制备方法。
技术方案:为实现上述发明目的,本发明采用的技术方案为:
异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物,其结构式为:
所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物的制备方法:在酸催化作用下,以无水乙醇为溶剂,异长叶烷基并嘧啶-2-胺(1a~1d)与2-羟基-1-萘甲醛缩合得到异长叶烷基并嘧啶-2-胺席夫碱类化合物(2a~2d)。
所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物的制备方法,包括以下步骤:
1)将0.01mol异长叶烷基并嘧啶-2-胺、0.01~0.015mol 2-羟基-1-萘甲醛、0.01~0.02mol乙酸、50~80mL乙醇依次加入配有搅拌器、温度计和回流冷凝器的三口烧瓶中,加热回流反应18~24h;
2)反应液冷却至室温,析出固体异长叶烷基并嘧啶-2-胺席夫碱粗产物;
3)将所得异长叶烷基并嘧啶-2-胺席夫碱粗产物在无水乙醇中进行重结晶,得到黄色粉末状异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物。
所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物作为荧光染料的应用。
有益效果:与现有的研究成果相比,本发明利用天然产物长叶烯衍生物异长叶烷基并嘧啶-2-胺为原料,制备了异长叶烷基并嘧啶-2-胺席夫碱类化合物;该类化合物在具有很好的固体荧光强度,在日光下表现为黄色,在紫外灯照射下可发出亮绿色或者亮黄色荧光,具有良好的荧光性能,可用作一类新型的有机小分子荧光染料,将具有广泛的应用。
附图说明
图1是异长叶烷基并嘧啶-2-胺席夫碱类化合物2a~2d的固态荧光光谱结果图;
图2是异长叶烷基并嘧啶-2-胺席夫碱类化合物2a~2d的固态光稳定性结果图;
图3是异长叶烷基并嘧啶-2-胺席夫碱类化合物2a~2d的固体荧光显微镜结果图。
具体实施方式
下面结合具体实施例对本发明做进一步的说明。
实施例1异长叶烷基并嘧啶-2-胺席夫碱类化合物的制备
异长叶烷基并嘧啶-2-胺席夫碱类化合物2a~2d的制备方法如下:
将1mmol异长叶烷基并嘧啶-2-胺(1a~1d)、1.2mmol 2-羟基-1-萘甲醛、5mmol乙酸和30mL乙醇,依次加入配有搅拌器、温度计和回流冷凝器的三口烧瓶中,加热回流反应24h,然后冷却至室温,析出黄色粗产物,再用无水乙醇进行重结晶,得到黄色粉末状的异长叶烷基并嘧啶-2-胺席夫碱产品(2a~2d)。
1-(((6,6,10,10-四甲基-4-(4′-氟苯基)-5,7,8,9,10,10α-六氢-6H-6α,9-桥亚甲基苯并[h]-2-喹啉基)亚胺基)甲基)萘-2-酚(2a),黄色粉末固体,得率为40.3%,m.p.285.4-286.1℃;1H NMR(400MHz,CDCl3)δ:0.71(s,3H),0.82(s,3H),1.07(s,3H),1.23-1.26(m,1H),1.35(d,J=8Hz,1H),1.53(s,3H),1.56-1.65(m,1H),1.71(d,J=12Hz,1H),1.79(d,J=12Hz,1H),1.86-1.88(m,1H),1.98-2.03(m,1H),2.38(d,J=20Hz,1H),2.56(s,1H),2.90(d,J=16Hz,1H),6.77(d,J=12Hz,1H),7.22-7.30(m,3H),7.48(t,J=8Hz,1H),7.54(d,J=8Hz,1H),7.67(d,J=8Hz,1H),7.70-7.74(m,2H),9.65(d,J=12Hz,1H),14.35(s,1H);13C NMR(100MHz,CDCl3)δ:23.20,24.95,25.64,26.38,28.68,30.26,33.03,37.56,40.21,44.81,48.02,55.33,58.30,108.80,115.43,115.65,119.07,122.27,124.37,127.02,127.30,128.95,129.63,131.68,133.91,134.65,141.09,145.80,154.76,162.47,164.95,165.59,171.05,184.92;HRMS(m/z):[M+H]+calcd for C34H34FN3O+H+,520.2764;found,520.2767.
1-(((6,6,10,10-四甲基-4-(4′-氯苯基)-5,7,8,9,10,10α-六氢-6H-6α,9-桥亚甲基苯并[h]-2-喹啉基)亚胺基)甲基)萘-2-酚(2b),黄色粉末固体,得率为42.8%,m.p.271.6-272.4℃;1H NMR(400MHz,CDCl3)δ:0.69(s,3H),0.80(s,3H),1.05(s,3H),1.20-1.26(m,1H),1.32-1.37(m,1H),1.50(s,3H),1.55-1.63(m,1H),1.69(d,J=12Hz,1H),1.77(d,J=8Hz,1H),1.84(s,1H),1.96-2.01(m,1H),2.35(d,J=16Hz,1H),2.54(s,1H),2.87(d,J=16Hz,1H),6.75(d,J=8Hz,1H),7.41-7.46(m,1H),7.48-7.53(m,3H),7.63-7.66(m,3H),7.92(d,J=8Hz,1H),9.62(d,J=12Hz,1H),14.35(s,1H);13C NMR(100MHz,CDCl3)δ:23.86,25.60,26.71,27.04,29.30,30.93,33.68,38.23,40.79,45.49,48.87,56.00,58.98,109.52,119.73,122.97,125.03,127.71,127.94,129.37,129.60,130.27,131.61,135.31,136.59,136.98,141.73,146.42,155.52,166.13,171.82,185.55;HRMS(m/z):[M+H]+calcd for C34H34ClN3O+H+,536.2469;found,536.2464.
1-(((6,6,10,10-四甲基-4-(对甲苯基)-5,7,8,9,10,10α-六氢-6H-6α,9-桥亚甲基苯并[h]-2-喹啉基)亚胺基)甲基)萘-2-酚(2c),黄色粉末固体,得率为45.5%,m.p.286.2-286.9℃;1H NMR(400MHz,CDCl3)δ:0.71(s,3H),0.82(s,3H),1.06(s,3H),1.23-1.28(m,1H),1.34(d,J=12Hz,1H),1.53(s,3H),1.57-1.63(m,1H),1,70-1.85(m,3H),1.98-2.03(m,1H),2.41-2.46(m,1H),2.49(s,3H),2.56(s,1H),2.91(d,J=16Hz,1H),6.78(d,J=8Hz,1H),7.29(d,J=8Hz,1H),7.36(d,J=8Hz,1H),7.47(t,J=4Hz,1H),7.54(d,J=8Hz,1H),7.61-7.68(m,3H),7.95(d,J=8Hz,1H),9.68(d,J=12Hz,1H),14.34(s,1H);13CNMR(100MHz,CDCl3)δ:21.96,23.51,25.31,25.96,26.71,29.00,30.62,33.35,37.91,40.56,45.12,48.58,55.73,58.66,109.05,119.44,122.72,124.59,127.34,127.71,129.22,129.49,129.88,129.92,135.10,135.48,140.23,141.27,146.31,155.06,167.05,171.04,185.20;HRMS(m/z):[M+H]+calcd for C35H37N3O+H+,516.3015;found,516.3038.
1-(((6,6,10,10-四甲基-4-(4′-(二甲基氨基)苯基)-5,7,8,9,10,10α-六氢-6H-6α,9-桥亚甲基苯并[h]-2-喹啉基)亚胺基)甲基)萘-2-酚(2d),黄色粉末固体,得率为46.3%,m.p.293.8-294.4℃;1H NMR(400MHz,CDCl3)δ:0.66(s,3H),0.78(s,3H),1.05(s,3H),1.17-1.21(m,1H),1.24(s,2H),1.31(d,J=8Hz,1H),1.48(s,3H),1.53-1.59(m,1H),1.66-1.69(m,3H),1.75-1.81(m,3H),1.94-1.99(m,1H),2.50(t,J=8Hz,2H),2.93(d,J=16Hz,1H),3.06(s,6H),6.75(d,J=12Hz,1H),6.80(d,J=12Hz,2H),7.45(t,J=8Hz,1H),7.51(d,J=8Hz,1H),7.63(d,J=8Hz,1H),7.69(d,J=12Hz,2H),7.93(d,J=8Hz,1H),9.68(d,J=12Hz,1H),14.31(s,1H);13C NMR(100MHz,CDCl3)δ:23.12,25.00,25.71,26.32,28.69,29.90,30.25,33.05,37.54,40.43,40.71,44.71,48.24,55.33,58.33,108.47,111.43,119.04,121.73,124.10,125.15,126.92,127.47,128.85,129.57,131.18,134.87,140.82,146.17,151.45,154.45,166.38,170.09,184.85;HRMS(m/z):[M+H]+calcd forC36H40N4O+H+,545.3280;found,545.3278.
实施例2异长叶烷基并嘧啶-2-胺席夫碱类化合物的荧光光谱测定
将0.5×10-6mol异长叶烷基并嘧啶-2-胺席夫碱2a~2d和1g KBr,先进行研磨混合均匀,然后采用红外溴化钾片的制备方法进行压片,得到4个溴化钾压片,最后用荧光光谱仪分别测定了这4个溴化钾压片的荧光光谱,结果如图1,随着苯环上取代基的供电子能力的增强,异长叶烷基并嘧啶-2-胺席夫碱的固体荧光强度逐渐增强。
实施例3异长叶烷基并嘧啶-2-胺席夫碱类化合物的光稳定性测定
将制得的异长叶烷基并嘧啶-2-胺席夫碱2a~2d的溴化钾压片,在紫外灯下连续照射140分钟,分别测定这4个混合的溴化钾压片在不同时间段的固体荧光光谱,结果如图2,异长叶烷基并嘧啶-2-胺席夫碱2a~2d的固体荧光强度不会随着时间而发生衰减,说明异长叶烷基并嘧啶-2-胺席夫碱2a~2d具有很好的光稳定性。
实施例4异长叶烷基并嘧啶-2-胺席夫碱类化合物的荧光显微测定
将一定量的异长叶烷基并嘧啶-2-胺席夫碱2a~2d放置于滤纸上,观察到样品为粉末状的黄色固体,为进一步观察样品的荧光性能,将其放置于荧光显微镜下,结果如图3所示。从图3可知:化合物2b和2c发出很强的绿色荧光,而化合物2d则发出显著的亮黄色荧光,说明异长叶烷基并嘧啶-2-胺席夫碱2b、2c和2d具有很好的荧光性能,可以作为有机小分子固体荧光材料的潜在原料。
Claims (5)
1.异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物,其特征在于,该类荧光化合物的结构式为:
式中,R为F、Cl、CH3、N(CH3)2。
2.权利要求1所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物的制备方法,其特征在于:以异长叶烷基并嘧啶-2-胺为原料,在酸催化作用下,与2-羟基-1-萘甲醛缩合得到异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物;其中,异长叶烷基并嘧啶-2-胺的结构式为:
式中,R为F、Cl、CH3、N(CH3)2。
3.根据权利要求2所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物的制备方法,其特征在于:以乙酸为催化剂、乙醇为溶剂。
4.根据权利要求2所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物的制备方法,其特征在于,包括以下步骤:
1)将0.01mol异长叶烷基并嘧啶-2-胺、0.01~0.015mol 2-羟基-1-萘甲醛、0.01~0.02mol乙酸、50~80mL乙醇依次加入配有搅拌器、温度计和回流冷凝器的三口烧瓶中,加热回流反应18~24h;
2)反应液冷却至室温,析出固体异长叶烷基并嘧啶-2-胺席夫碱粗产物;
3)将所得异长叶烷基并嘧啶-2-胺席夫碱粗产物在无水乙醇中进行重结晶,得到黄色粉末状异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物。
5.权利要求1所述的异长叶烷基并嘧啶-2-胺席夫碱类荧光化合物作为荧光染料的应用。
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