CN108033982A - 一种聚集诱导磷光增强Re(I)配合物及其制备方法 - Google Patents
一种聚集诱导磷光增强Re(I)配合物及其制备方法 Download PDFInfo
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- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
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Abstract
本发明提供了一种利用Suzuki偶联反应制备聚集诱导磷光增强Re(I)配合物的实验方法，所合成的聚集诱导磷光增强Re(I)配合物的分子结构及其制备路线如式(I)所示；本发明所合成的Re(I)配合物不但具有在1,10‑邻菲罗啉衍生物配体的2‑,9‑位连有两个空间位阻较大基团的特点，而且它们还表现出聚集诱导发光增强特性。
Description
技术领域
本发明属于过渡金属磷光Re(I)配合物材料领域，具体涉及一种聚集诱导磷光增强Re(I)配合物及其制备方法。
背景技术
具有制备条件简单，热稳定性好，激发态寿命长等特点的磷光Re(I)配合物由于在有机电致发光器件、生物标签和光学传感等众多领域都具有极大的应用潜力。由于2-位和9-位双功能化的1,10-邻菲罗啉衍生物会产生较大的空间位阻效应，很难利用在InorganicChemistry中2007年第46期第6155页题为“Synthesis,Structural Characterization,andElectrophosphorescent Properties of Rhenium(I)Complexes Containing Carrier-Transporting Groups(含有载流子传输基团的Re(I)配合物的合成、结构表征和电致磷光性质)”的文献所涉及的方法制备以2-,9-位双功能化的1,10-邻菲罗啉衍生物为配体的磷光Re(I)配合物。所以目前对以1,10-邻菲罗啉衍生物为配体的磷光Re(I)配合物的化学修饰主要发生在1,10-邻菲罗啉的3-、5-、6-或8-位。
经过对现有技术的检索发现，在Journal of Materials Chemistry中2007年第17期第4255页题为“Solution processable phosphorescent rhenium(I)dendrimers(可以通过溶液法进行处理的枝形磷光Re(I)配合物”)和在RSC Advances中2013年第3期第23963页题为“Rhenium(I)phenanthrolines bearing electron withdrawingCF3substituents:synthesis,characterization and biological evaluation(含吸电子取代基CF3的铼(I)配合物:合成，表征与生物评价)”两篇文献曾先后利用两步法在1,10-邻菲罗啉衍生物的2-,9-位同时引入3,5-二(2-乙基己氧基苯基)苯基、3-CF3C6H4和4-CF3C6H4，进而合成出相应的Re(I)配合物。由于上述文献的合成技术都涉及到易燃易爆的有机锂试剂——正丁基锂溶液，所以相应的制备过程具有较大的安全隐患。
利用Suzuki偶联反应向以2,9-二溴-1,10-邻菲罗啉衍生物为配体的磷光Re(I)配合物中引入有机基团，不但可以充分利用Suzuki偶联反应对底物适应性及官能团容忍性的优点，还能避免使用有机锂试剂所带来的潜在危险。对扩展磷光Re(I)配合物的分子结构设计与性质研究具有重要意义，而且目前还没有关于这方面的研究报道。
发明内容
式(I)中，R1为C1-C10烷基、芳基或-H；
R2，R3和R4独立地选自为C1-C10烷基、芳基、-H或有机硅自由基。
鉴于此，本发明为实现上述目的而提出的技术方案如下：向溶有[(2,9-二溴-1,10-邻菲罗啉)Re(CO)3Br]和芳香硼酸(包括4-甲基苯硼酸、3，5-二苯基硼酸和4-三苯基硅基苯硼酸等)的正丙醇溶液中依次加入醋酸钯，三苯基膦和碳酸钾，惰性气体保护下回流，TLC检测完全后冷却至室温并用碳酸氢钠淬灭反应，用二氯甲烷萃取后有机相用无水硫酸钠干燥，蒸除有机溶剂所得到的固体经柱层析法提纯后得到物黄色固体粉末。
在所述方案中，所用惰性气体是氮气或氩气。
在所述方案中，所用碳酸钾是2mol/L的水溶液；碳酸氢钠是5％的水溶液；回流温度为115℃；反应时间为24～36小时；硅胶柱层析洗脱液为：乙酸乙酯和石油醚(体积比为1/3～1/2)。
本发明的优点在于：所采用的Suzuki偶合反应具有反应物适应性好，安全性高的特点；所合成的Re(I)配合物具有聚集诱导磷光增强特性。
附图说明
图1为本发明所涉及的聚集诱导磷光增强Re(I)配合物材料的制备方法。
图2为本发明的实施例得到的浓度约为10-5mol/L的Re-1在不同比例的THF/H2O混合溶剂中的发射光谱图。
图3为本发明的实施例得到的浓度约为10-5mol/L的Re-2在不同比例的THF/H2O混合溶剂中的发射光谱图。
图4为本发明的实施例得到的浓度约为10-5mol/L的Re-3在不同比例的THF/H2O混合溶剂中的发射光谱图。
具体实施方式
本发明提供了一种聚集诱导磷光增强Re(I)配合物材料及其制备方法，其中聚集诱导磷光增强Re(I)配合物的结构如式(I)所示：
结构式(I)中，R1为C1-C10烷基、芳基或-H；
R2，R3和R4独立地选自为C1-C10烷基、芳基、-H或有机硅自由基。
为了更好地理解本发明的内容，结合以下具体实施例和附图对本发明作进一步的详细说明，实施例中所用试剂均为市售。但本发明的保护内容不局限于以下实施例。实施本发明的过程、条件、试剂、试验方法等，除以下专门提及的内容之外，均为本领域的普遍知识，本发明没有特别限制内容。
实施例1：结构式(I)中聚集诱导磷光增强Re(I)配合物Re-1的合成
Re(CO)3(Br2Phen)Br(0.172g,0.25mmol),4-甲基苯硼酸(0.045g,0.55mmol),醋酸钯(0.3％摩尔当量),三苯基膦(0.9％摩尔当量)和1.0mL碳酸钾水溶液(2.0mol/L,2.0mmol)先后加入到20mL正丙醇后，在氮气保护下反应24小时。反应体系降到室温后用浓度为5.0％的碳酸氢钠水溶液猝灭反应。二氯甲烷萃取有机相后用无水硫酸钠干燥。蒸除溶剂后经硅胶柱层析(洗脱液为乙酸乙酯和石油醚，v/v＝1/3)提纯得到0.053g Re-1，产率为29.8％.1HNMR(CDCl3,400MHz,ppm):8.529(d,2H,J＝8.28Hz),8.022(s,2H),7.916(d,2H,J＝8.24Hz),7.661(s,4H),7.391(d,4H,J＝7.6Hz),2.486(s,6H).13C NMR(CDCl3,400MHz,ppm):193.17,192.73,164.61,148.65,142.48,140.61,140.21,138.96,138.29,137.91,132.75,129.82,129.53,129.23,126.70,126.47,125.95,123.16,118.78,23.40.FT-IR(KBr,cm-1):3060,2034,1926,1614,1266,1030,703,636。
实施例2：结构式(I)中聚集诱导磷光增强Re(I)配合物Re-2的合成
Re(CO)3(Br2Phen)Br(0.172g,0.25mmol),3,5-二苯基苯硼酸(0.151g,0.55mmol),醋酸钯(0.3％摩尔当量),三苯基膦(0.9％摩尔当量)和1.0mL碳酸钾水溶液(2.0mol/L,2.0mmol)先后加入到20mL正丙醇后，在氮气保护下反应28小时。反应体系降到室温后用浓度为5.0％的碳酸氢钠水溶液猝灭反应。二氯甲烷萃取有机相后用无水硫酸钠干燥。蒸除溶剂后经硅胶柱层析(洗脱液为乙酸乙酯和石油醚，v/v＝1/3)得到0.051g Re-2，产率为20.8％.1H NMR(CDCl3,400MHz,ppm):8.752(d,2H,J＝8.24Hz),8.088(s,2H),8.01(d,4H,J＝6.72Hz),7.895(d,4H,J＝14.52Hz),7.762(m,8H),7.459(t,8H),7.375(t,4H).13C NMR(CDCl3,400MHz,ppm):192.68,164.64,148.40,142.87,142.80,142.04,140.38,137.97,130.16,128.86,127.91,127.79,127.74,127.63,127.46,127.28,127.16,126.92,126.84.FT-IR(KBr,cm-1):2934,2035,1940,1278,1620,1024,707,631。
实施例3：结构式(I)中聚集诱导磷光增强Re(I)配合物Re-3的合成
Re(CO)3(Br2Phen)Br(0.172g,0.25mmol),4-三苯基硅基苯硼酸(0.209g,0.55mmol),醋酸钯(0.3％摩尔当量),三苯基膦(0.9％摩尔当量)和1.0mL碳酸钾水溶液(2.0mol/L,2.0mmol)先后加入到20mL正丙醇后，在氮气保护下反应36小时。反应体系降到室温后用浓度为5.0％的碳酸氢钠水溶液猝灭反应。二氯甲烷萃取有机相后用无水硫酸钠干燥。蒸除溶剂后经硅胶柱层析(洗脱液为乙酸乙酯和石油醚，v/v＝1/3)得到0.077g Re-3，产率为25.6％。1HNMR(CDCl3,400MHz,ppm):8.544(d,2H,J＝8.24Hz),8.037(s,2H),7.929(d,2H,J＝8.24Hz),7.766(s,8H),7.624(d,12H,J＝7.2Hz),7.423(m,18H).13C NMR(CDCl3,400MHz,ppm):192.72,164.48,148.56,142.54,138.01,137.32,136.47,133.74,130.02,129.71,129.24,128.59,127.96,127.19,126.75.FT-IR(KBr,cm-1):3073,2356,2033,1923,1615,1266,1108,1033,704,636。
以上所述仅是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。
Claims (3)
1.一种由式(I)所示的利用Suzuki偶联反应合成的聚集诱导磷光增强Re(I)配合物材料，其特征在于配体的2-,9-位同时具有空间位阻较大的基团；具有聚集诱导磷光增强现象，
式(I)中，R1为C1-C10烷基、芳基或-H；
R2，R3和R4独立地选自为C1-C10烷基、芳基、-H或有机硅自由基。
2.一种按权利要求1所述Re(I)配合物的制备方法，其特征在于：前驱体Re(CO)3[Phen(R1)2Br2]Br在正丙醇中与芳香硼酸衍生物混合后，先后加入醋酸钯、三苯基磷、碳酸钾，充分反应后用碳酸氢钠淬灭反应，二氯甲烷萃取后有机相经无水硫酸钠干燥后再蒸出有机溶剂，最后硅胶柱层析后得到黄色固体粉末。
3.根据权利要求2所述的制备方法，其特征在于：反应需要在氮气保护下不间断搅拌，碳酸钾是2mol/L的水溶液；碳酸氢钠是5％的水溶液；反应温度为115℃；反应时间为24～36小时；柱层析所用洗脱液为乙酸乙酯/石油醚混合物，比例范围为1/3～1/2。
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| WO2003079737A2 (en) * | 2002-03-15 | 2003-09-25 | Isis Innovation Limited | Rhenium compounds and their use in electroluminescent vorrichtungen |
| CN102891258A (zh) * | 2011-07-18 | 2013-01-23 | 吉林师范大学 | 一种基于Re(I)配合物磷光材料的有机光探测器件 |
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