CN110194759B - 二苯并碲吩类有机室温磷光材料及其合成方法 - Google Patents
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Abstract
Description
技术领域
本发明涉及一种二苯并碲吩化合物及其制备方法,并观察到二苯并碲吩类化合物的固体具有室温磷光特性。
背景技术
有机发光材料在有机发光二极管、生物成像、分子探针等领域具有广泛的用途。与荧光相比,磷光发射由于其独特的发光性质在众多领域更具应用优势。其中,室温磷光材料(RTP)尤其具有吸引力。然而,室温发出磷光的材料主要是含有贵金属的配位络合物,由于这些有机金属化合物价格昂贵且毒性较大,因此需要开发新型的纯有机室温磷光材料。到目前为止,具有室温磷光特性的纯有机材料尚很少,参见:Chem.Commun.2015,51,10988;Adv.Mater.2012,24,3169。
开发纯有机室温磷光材料,设计分子时需要仔细考虑两个重素:1)通过系间穿越(ISC)促进自旋禁阻的单线态到三线态激发态的跃迁2)尽可能多地抑制非辐射弛豫途径。研究表明,引入重原子可以有效促进分子的系间穿越(ISC),从而有利于磷光的发射。碲元素属于硫族元素,但相对于较轻的硫族元素(硫和硒),碲具有独特的性质,如强重原子效应、可形成稳定的高价碲化合物、碲和碲之间以及碲和其它杂原子间容易形成强烈的分子间相互作用、含碲芳香化合物具有较低的带隙等。在有机骨架中引入碲原子,由于其重原子效应可以促进系间穿越,从而可能产生磷光。2014年Rivard等人报道了硼取代的碲吩具有聚集诱导的室温磷光特性,参见Angew.Chem.Int.Ed.2014,53,4587。后来他们发现了一些取代的碲吩具有类似的性质,参见ACS Appl.Mater.Interfaces 2018,10,12124。但目前为止,具有RTP特性的含碲分子主要是单环的碲吩类化合物,其结构式如下:
文献中曾报道的二苯并碲吩合成方法主要有以下几种:
二苯并碲吩可以从二苯并噻吩的二氧化合物和碲粉共热得到。该方法原料不易得到(尤其是含取代基的结构),反应温度高和产率很低。(参考:Recl.Trav.Chim.Pays-Bas,1937,56,627.doi:10.1002/recl.19370560704)。
1975年,J.D.McCullough合成了无取代的二苯并碲吩,从溴化芳基和正丁基锂出发,四氯化碲为碲源,经过4步合成。该反应操作步骤复杂,需要使用活泼的丁基锂试剂,也导致官能团兼容性差。(见参考文献:Inorganic Chemistry,1975,14,2285)
1991年,Seiji Suga报道了从二溴取代的芳基和叔丁基锂出发,碲粉为碲源合成二苯并碲吩化合物。该反应产率较低,同样需要使用对水和空气敏感的危险试剂叔丁基锂,操作复杂,官能团兼容性差。(见参考文献:J.Heterocyclic Chem,1991,28,433)
2017年,Yoshikai等人报道了下面的合成方法合成了二苯并碲吩类化合物,该方法同样操作步骤繁琐,需要使用活泼的金属试剂。(见参考文献:Chem.Sci.,2017,8,4527)
1995年,Suzuki,H和Nakamura,T.报道了从二碘化合物和碲粉在原位生成的Te-Cu催化作用下,合成了二苯并碲吩类化合物(J.Org.Chem.1995,60,5274)。该方法虽然不需要使用活泼的金属锂或格式试剂,但该反应需要使用二碘化合物为底物,反应使用的Te-Cu催化剂需要从不稳定的Na2Te原位制备。
综上所述,碲吩等化合物的合成方法大多数反应存在步骤较长、操作繁琐、产率较低、反应条件较苛刻和官能团兼容性差等缺点,严重制约了二苯并碲吩类化合物的应用研究。因此,开发新的二苯并碲吩的合成方法无疑会促进其在材料领域的应用。
发明内容
本发明的目的之一在于提供一种具有室温磷光特性的二苯并碲吩类有机功能分子。
本发明的目的之二在于提供一种上述的二苯并碲吩类有机功能分子的制备方法。
为达到上述目的,本发明方法采用的机理如下:
R1,R2=氢,烷基,芳基,烷氧基,卤素,氰基,酯基,三氟甲基,乙酰胺基等。
该合成方法其特征在于该方法具有如下步骤:氮气保护下,碘鎓盐和碲粉按照1:(1.0~5.0)的摩尔比加入到Schlenk管中,然后加入DMSO和2-甲基吡啶的混合液中(体积比为1:0.1~1:10),加热至80~150℃,反应体系除去溶剂后所得粗产物,再进行分离提纯得到二苯并碲吩类化合物。
碲吩类化合物是一种重要的有机功能材料,其在有有机太阳能电池(如:J.Am.Chem.Soc.2015,137,1314)及有机发光材料(如Angew.Chem.Int.Ed.2014,53,4587)等领域具有重要应用。本专利合成的二苯并碲吩类化合物是一类具有重要应用潜力的有机功能分子。
我们发现合成的二苯并碲吩化合物具有固体的室温磷光特性,其特征为固体在环境条件下(室温和空气中)呈现磷光的特性:该类化合物的粉末和晶体在250~400nm紫外光的激发下,具有明显的发光现象,发射波长为400~700nm;经瞬态光谱仪分析,其发光寿命为1~50微秒。该性质为该类化合物在有机发光材料和生物成像等方面的应用打下了基础。
附图说明
图1为本发明的化合物的紫外可见吸收光谱(2×10-5M in THF溶液);
图2为本发明的化合物的固体照片(365nm的紫外灯下);
图3为本发明的化合物的固体粉末的发射光谱(激发波长为350nm,狭缝均为3nm);
图4为本发明化合物发光寿命的测定;
图5为部分化合物在365nm紫外灯下数码照片。
具体实施方式
实施例一:二苯并[b,d]碲酚
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入128.4mg二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃,反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE)纯化,得到62mg产物,产率73%。熔点:94-95℃,室温365nm下发射黄绿色磷光。所得产物的表征数据如下:IR(KBr,cm-1):3030,1701,1550,1416,733;1H NMR(500MHz,CDCl3):δ8.11(dd,J=8.0,1.3Hz,1H),7.91–7.85(m,1H),7.46(ddd,J=8.2,7.2,1.2Hz,1H),7.30(ddd,J=7.7,7.2,1.3Hz,1H);13CNMR(125MHz,CDCl3):δ143.8,132.4,128.6,126.7,125.5,124.5;LRMS(DART)calcd for C12H8Te[M]+282.0。
实施例二:3-甲氧基二苯并[b,d]碲酚
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入137.4mg 3-甲氧基二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃,反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE:EA=200:1)纯化,得到71mg产物,产率为76%。熔点:168-169℃,室温365nm下发射黄色磷光。所得产物的表征数据如下:IR(KBr,cm-1):2923,2856,1585,1454,1253,1217,1023,825,759,719;1HNMR(500MHz,CDCl3):δ7.96(m,2H),7.83(d,J=8.0Hz,1H),7.41(t,J=8.1Hz,1H),7.38(m,1H),7.25(m,1H),7.03(dd,J=8.7Hz,J=5.5Hz,1H),3.8(s,3H);13C NMR(125MHz,CDCl3):δ158.7,143.9,137.5,132.5,129.9,127.5,126.0,125.8,125.2,124.0,116.1,114.0,55.6;HRMS(DART)calcdfor C13H10OTe[M]+311.9794,found 311.9790。
实施例三:3-甲基二苯并[b,d]碲酚
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入135.9mg 3-甲基二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃,反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE)纯化,得到65.6mg 3-甲氧基二苯并[b,d]碲酚,其结构式为,产率为74%,熔点:68-69℃,室温365nm下发射黄色磷光。所得产物的表征数据如下:IR(KBr,cm-1):2921,1587,1430,1231,1201,806,748,708;1HNMR(500MHz,CDCl3)δ8.05(dd,J=8.0,1.3Hz,1H),7.98(d,J=8.1Hz,1H),7.89-7.81(m,1H),7.75-7.65(m,1H),7.43(d,J=1.1Hz,1H),7.31-7.23(m,2H),2.43(s,3H);13C NMR(125MHz,CDCl3)δ144.2,141.8,137.1,132.9,132.7,128.8,128.2,127.2,126.6,125.8,124.4,124.4,21.5;HRMS(ESI)m/z calcd for C13H10Te+(M)+295.9839,found 295.9838。
实施例四:甲基二苯并[b,d]碲酚-3-羧酸甲酯
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入145.8mg 3-(甲氧基羰基)二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃,反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE:EA=20:1)纯化,得到57.3mg甲基二苯并[b,d]碲酚-3-羧酸甲酯,产率为57%,熔点:128-129℃。室温365nm下发射微弱的磷光。所得产物的表征数据如下:IR(KBr,cm-1):3050,2986,2941,1702,1583,1427,1378,1282,1243,1105,963,911,744,522;1H NMR(500MHz,CDCl3):δ8.58(s,1H),8.17(d,J=12.4Hz,1H),8.14(s,1H),8.10(d,J=8.3Hz,1H),7.92(d,J=7.8Hz,1H),7.49(t,J=8.2Hz,1H),7.36(t,J=8.1Hz,1H),3.96(s,3H);13CNMR(125MHz,CDCl3):δ166.8,147.9,143.0,134.2,132.8,130.5,128.6,128.1,127.9,126.9,126.0,125.6,124.2,52.4;HRMS(DART)calcd for C14H10O2Te[M]+339.9743,found 339.9738。
实施例五:3-溴二苯并[b,d]碲酚
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入152mg 3-溴二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃。反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE)纯化,得到74.9mg 3-溴二苯并[b,d]碲酚,产率为70%,熔点:81-82℃,室温365nm下呈黄色光。所得产物的表征数据如下:IR(KBr,cm-1):3039,2916,1562,1430,1368,1280,1234,1069,1027,860,751,710,680,566;1HNMR(400MHz,CDCl3)δ8.06(d,J=8.0Hz,1H),7.93(d,J=8.5Hz,1H),7.56(d,J=10.4Hz,1H),7.51-7.40(m,1H),7.39-7.28(m,1H);13C NMR(125MHz,CDCl3):143.1,143.0,134.8,132.6,130,4,129.2,128.8,127,4,126.0,125.7,124.8,120.9;HRMS(ESI)m/z calcd forC12H7BrTe+(M)+359.87879,found 359.87836。
实施例六:3,7-二溴二苯并[b,d]碲酚
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入175.1mg 3,7-二溴二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃,反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE)纯化,得到96.2mg 3,7-二溴二苯并[b,d]碲酚,产率为73%,熔点为213-214℃,室温365nm下发射橙色光磷光。所得产物的表征数据如下:IR(KBr,cm-1):2922,2858,1723,1559,1436,1361,1259,1079,863,804,702 1H NMR(500MHz,CDCl3):δ7.98(s,2H),7.87(d,J=8.5Hz,2H),7.56(d,J=8.5Hz,2H);13C NMR(125MHz,CDCl3):δ141.9,134.8,130.4,128.4,125.7,121.3.HRMS(DART)calcd forC12H6Br2TeO[M+O]+453.7848,found 453.7861。
实施例七:二甲基二苯并[b,d]碲吩-3,7-二羧酸酯
一种制备上述二苯并碲酚化合物的方法,其特征在于具体步骤如下:氮气保护下,在25mL Schlenk管中加入163.1mg 3,7-双(甲氧基羰基)二苯并[b,d]碘-5-鎓三氟甲磺酸盐和58mg碲粉,在通氮气的情况下加入2.0mL DMSO和1.0mL 2-甲基吡啶,加热至120℃,反应12h。冷却后倒入10mL水中,用45mL二氯甲烷萃取产物,饱和食盐水洗,无水硫酸钠干燥,用旋转蒸发仪去掉溶剂,得到粗产物;粗产物用柱层析(PE:EA=10:1)纯化,得到67.8mg二甲基二苯并[b,d]碲吩-3,7-二羧酸酯,其结构式为,产率为58%,熔点:225-226℃,室温365nm下发射橙色光磷光。所得产物的表征数据如下:IR(KBr,cm-1):3397,3070,2940,1712,1583,1431,1383,1277,1111,975,836,755,695;2935,2845,1711,1582,1462,1382,1276,1237,1109,972,834,754;1H NMR(500MHz,CDCl3):δ8.60(d,J=1.5Hz,2H),8.20(d,J=8.3Hz,2H),8.13(dd,J=8.4,1.6Hz,2H),3.97(s,6H);13C NMR(125MHz,CDCl3):δ166.6,146.7,134.3,130.3,128.9,127.1,125.3,52.5.HRMS(DART)calcd for C16H12O4Te[M]+397.9798,found397.9790。
实施例八:吸收光谱及磷光性能测试
样品制备:实施例一制备的化合物,首先溶解于光学纯的THF溶液中(浓度为2×10-5M),通过紫外可见分光光度计测试其紫外吸收光谱,其谱图如图1所示。
然后分别以345nm,280nm和250nm为激发波长,测试其溶液的发射光谱,该化合物溶液状态没有明显的发光。
将该化合物固体研成粉末,在365纳米下其发射出绿色磷光,其数码照片如图2所示。
分别以365nm和320nm测试其固体发光光谱,其谱图图3所示。
为证明其磷光特性,我们对其发光寿命进行了测试,其发光寿命为τ1=1.3μs,τ2=10.3μs,其衰减曲线如图4所示。
其它化合物也观察到了类似的现象,部分化合物的365nm紫外灯下数码照片如图5所示。
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