CN107324965A - 一种蒽衍生物的制备方法 - Google Patents

一种蒽衍生物的制备方法 Download PDF

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CN107324965A
CN107324965A CN201710599223.8A CN201710599223A CN107324965A CN 107324965 A CN107324965 A CN 107324965A CN 201710599223 A CN201710599223 A CN 201710599223A CN 107324965 A CN107324965 A CN 107324965A
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胡文平
甄永刚
柏晗
刘洁
舒志斌
董焕丽
江浪
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Abstract

本发明公开了一种蒽衍生物的制备方法。所述蒽衍生物的结构式如式Ⅰ所示，其制备方法包括下述步骤：使式Ⅱ所示化合物与锌在碱性条件下进行反应，得到式Ⅰ所示的蒽衍生物。该方法克服了常规合成方法中原料来源困难、价格昂贵、生产设备要求高、安全环保压力大、不利于工业化生产的缺点。具有简单高效、环境友好、原料价格廉价、试剂用量降低的优点；对所用原料、试剂和溶剂要求不高，化学纯即可；普适性高，重复性好。

Description

一种蒽衍生物的制备方法
技术领域
本发明属于化工领域，具体涉及一种蒽衍生物的制备方法。
背景技术
蒽类化合物由于具有高荧光量子产率、分子结构的易修饰性及高热稳定性，使得蒽及其衍生物在有机光电材料领域有重要的地位和应用前景。例如，有机半导体领域，包括有机场效应晶体管、有机发光二极管和有机光伏材料等，其中特别是有机场效应晶体管材料，由于其优异的半导体性能，引起半导体工业界的关注。
然而，目前取代蒽衍生物主要是通过引入卤原子、烷基等基团，进一步通过偶联反应在相应的位置引入基团，其申请的专利有US2008012006A1。其合成路线如图1所示。
卤代蒽因合成条件苛刻而使价格持高不下，这就限制了该制备路线在低成本大规模制备取代蒽衍生物方面的应用。因此，发展绿色的制备工艺，降低成本、提高其产率、缩短生产周期、降低能耗、减少污染物排放，是材料制备和新材料的应用的基础保障。
发明内容
本发明的一个目的是提供一种蒽衍生物的制备方法，以降低成本，提高产率。
为了实现上述目的，本发明提供了一种式Ⅰ所示的蒽衍生物的制备方法，包括下述步骤：使式Ⅱ所示化合物与锌在碱性条件下进行反应，得到式Ⅰ所示的蒽衍生物。
具体合成路线图如图2所示。
式Ⅰ中，R1、R2、R3、R4、R5、R6、R7各自独立地表示氢、C1-C48的烷基、含有S、N和O中至少一种杂原子的C1-C48的烷基、取代或未取代的C6-C48的芳基、取代或未取代的C5-C48的含氧芳基、取代或未取代的C5-C48的含硫芳基、取代或未取代的C5-C48的含硒芳基、取代或未取代的C5-C48的含氮芳基、取代或未取代的C5-C48的含磷芳基、取代或未取代的C5-C48的含氮杂环基、取代或未取代的C5-C48的含硅杂环基、取代或未取代的C6-C48的卤代芳基、卤素、羟基、对甲苯磺酸酯基(-OTs)或三氟甲磺酸酯基(OTf)；其中，所述C6-C48的卤代芳基中的卤代表示氟代、氯代、溴代或碘代；被取代基团中的取代基为C1-C24的烷基或C1-C24烷氧基。
优选地，R1、R2、R3、R4、R5、R6各自独立地表示氢、C1-C5的烷基或C1-C5的烷氧基；
R7选自C1-C5的烷基，或，取代或未取代的下述基团中的任意一种：苯基、萘基、蒽基、吡啶基、并四苯基、并五苯基、噻吩基、苯并噻吩基、硫杂蒽、硫杂并四苯、硫杂并五苯、苯并吡咯基、氮杂蒽、氮杂并四苯、氮杂并五苯；其中，被取代的基团中的取代基可为C1-C24的烷基或C1-C24烷氧基。
在上述反应中，所述碱性条件由下述至少一种碱提供：氢氧化锂、氢氧化钠、氢氧化钾、氢氧化钡、碳酸锂、碳酸钠、碳酸钾和碳酸铯；优选为氢氧化钠，其水溶液的质量浓度为5～25％。
所述式Ⅱ所示化合物、锌及碱的投料摩尔比为1:(1～30):(1～50)，优选为1:(10～30):(10～30)。
所述反应在空气或惰性气氛中进行；所述惰性气氛为氮气气氛或氩气气氛。
所述反应在溶剂中进行，所述溶剂选自下述至少一种：乙腈、甲醇、乙醇、异丙醇、仲丁醇、叔丁醇、3-戊醇、2-戊醇、叔戊醇、2-甲基丁醇、3-甲基-3-戊醇、乙二醇、乙二醇单甲醚、二氯甲烷、三氯甲烷、1,4-二氧六环、苯、甲苯、二甲苯、乙酸乙酯、二甲基亚砜和四氢呋喃，优选为乙醇和/或异丙醇。
所述反应的反应温度为25℃至回流温度，优选为70℃至回流温度；反应时间为1～120小时，优选为48～72小时。
可选择地，在上述反应结束后，还可对制得的式Ⅰ所示化合物进行分离提纯。一种示例性的分离提纯的方法包括如下步骤：(1)蒸去溶剂；(2)加入剩余物体积1～10倍体积的水和剩余物体积1～5倍的可溶性溶剂，萃取并分出有机层，水层用1～5倍体积的可溶性溶剂萃取；(3)合并有机层，经无水硫酸钠干燥，浓缩，可进一步通过重结晶或升华来提纯。
本发明中所使用的原料式Ⅱ所示化合物，是由式Ⅲ所示的2,6位氨基取代的蒽醌类化合物通过重氮盐、桑德迈尔反应以及Suzuki偶联反应获得，具体合成方法可参考文献：Chem.Commun.,2013,49,1199；J.Mater.Chem.C,2015,3,3068。具体合成路线如图2所示。
式Ⅲ中R1、R2、R3、R4、R5、R6的定义同式Ⅱ。
本发明提供的蒽衍生物的制备方法，克服了常规合成方法中原料来源困难、价格昂贵、生产设备要求高、安全环保压力大、不利于工业化生产的缺点。
本发明的优点在于：
1、本系列反应路线具有简单高效、环境友好、原料价格廉价、试剂用量降低的优点；对所用原料、试剂和溶剂要求不高，化学纯即可；普适性高，重复性好。
2、不同取代的烷基或芳香基团可以使得蒽衍生物的物理性能多样化，可以推广应用到其他各种取代基的蒽类衍生物的合成。
3、其衍生化的蒽类化合物可应用于有机功能材料领域，并为实现有机功能材料的大规模生产提供了一种简单易行的合成路线。
附图说明
图1为US2008012006A1专利中2,6位取代蒽衍生物合成路线图。
图2为式Ⅱ所示化合物的的合成路线图。
图3为本发明提供的2,6位取代蒽衍生物的合成路线图。
具体实施方式
下面通过具体实施例对本发明的方法进行说明，但本发明并不局限于此，凡在本发明的精神和原则之内所做的任何修改、等同替换和改进等，均应包含在本发明的保护范围之内。
下述实施例中所使用的实验方法如无特殊说明，均为常规方法。
下述实施例中所用的材料、试剂等，如无特殊说明，均可从商业途径得到。
实施例1、2,6-二苯基蒽(式Ⅰ中R1-R6均为氢，R7为苯基的化合物)的制备
将2,6-二苯基-9,10-蒽醌(5.08g,14.1mmol)、锌(20eq.)，在氩气保护下，依次加入乙醇100mL、质量浓度为10％的NaOH溶液100mL和异丙醇100mL，升温至95℃反应72小时。冷却至室温过滤，滤饼用水清洗后使用质量浓度10％的稀盐酸溶液除去滤饼中过量的锌，接着依次用水、二氯甲烷、甲醇清洗，烘干，用氯萘可重结晶可得2,6-二苯基蒽，产率约为85％。
其结构确认数据如下：MS(EI):m/z＝330(100)(M+)；1H NMR(400MHz,CDCl3)δ(ppm):8.50(s,2H),8.21(s,2H),8.10(d,2H),7.78(m,6H),7.52(t,4H),7.40(m,2H)；元素分析C26H18(％):C 94.48(94.51),H 5.45(5.49)。
经结构确证，所得化合物确为目标产物。
实施例2、2,6-二(4-吡啶基)蒽(式Ⅰ中R1-R6均为氢，R7为4-吡啶基的化合物)的制备
将2,6-二(4-吡啶基)-9,10-蒽醌(3.62g,10mmol)、锌(20eq.)，在氩气保护下，加入乙醇100mL，质量浓度为10％NaOH溶液100mL，升温至100℃反应48小时。冷却至室温过滤，滤饼用大量的水清洗，接着用稀盐酸除去过量的锌，再用水和二氯甲烷依次清洗，可进一步升华提纯得2,6-二(4-吡啶基)蒽，产率约为78％。
其结构确认数据如下：MS(EI):m/z＝332(100)(M+)；1H NMR(400MHz,CDCl3)δ(ppm):8.75(d,J＝5.7Hz,4H),8.57(s,2H),8.33(s,2H),8.17(d,J＝8.8Hz,2H),7.79(dd,J＝8.8,1.4Hz,2H),7.70(d,J＝6.0Hz,4H)。
经结构确证，所得化合物确为目标产物。
实施例3、2,6-二(2-萘基)蒽(式Ⅰ中R1-R6均为氢，R7为萘基的化合物)的制备
将2,6-二(2-萘基)-9,10-蒽醌(4.30g,10mmol)、锌(20eq.)，在氩气保护下，加入乙醇100mL，10％NaOH 100mL，升温至95℃反应96小时。冷却至室温过滤，滤饼用大量的水清洗，用质量浓度10％的稀盐酸除去过量的锌，滤饼再依次用水和甲醇清洗，最终升华提纯得2,6-二(4-吡啶基)蒽，产率约为72％。
其结构确认数据如下：MS(EI)m/z:430(M+)；1H NMR(400MHz,CDCl3):8.60(s,2H),8.40(s,2H),8.28(s,2H),8.21(d,4H),8.03(m,10H),7.58(m,4H)；元素分析C34H22(％):C:94.50(94.85),H:5.45(5.15)。
实施例4、2,3,6,7-四甲基蒽(式Ⅰ中R1、R3、R4、R6均为氢，R2、R5、R7均为甲基的化合物)的制备
将2,3,6,7-四甲基-9,10-蒽醌(2.64g,10mmol)、锌(20eq.)，在氩气保护下，加入乙醇100mL，10％NaOH 100mL，升温至90℃反应72小时。冷却至室温过滤，滤饼用大量的水清洗，用质量浓度10％的稀盐酸除去过量的锌，滤饼再依次用水和甲醇清洗，最终提纯得2,3,6,7-四甲基蒽，产率约为93％。
其结构确认所得化合物确为目标产物，核磁数据如下：1H NMR(500MHz,CDCl3,300K)δ(ppm):8.15(s,2H),7.70(s,4H),2.45(s,12H)。

Claims (8)

1.式Ⅰ所示的化合物的制备方法，包括下述步骤：使式Ⅱ所示化合物与锌在碱性条件下进行反应，得到式Ⅰ所示的化合物；
式Ⅰ中，R1、R2、R3、R4、R5、R6、R7各自独立地表示氢、C1-C48的烷基、含有S、N和O中至少一种杂原子的C1-C48的烷基、取代或未取代的C6-C48的芳基、取代或未取代的C5-C48的含氧芳基、取代或未取代的C5-C48的含硫芳基、取代或未取代的C5-C48的含硒芳基、取代或未取代的C5-C48的含氮芳基、取代或未取代的C5-C48的含磷芳基、取代或未取代的C5-C48的含氮杂环基、取代或未取代的C5-C48的含硅杂环基、取代或未取代的C6-C48的卤代芳基、卤素、羟基、对甲苯磺酸酯基(-OTs)或三氟甲磺酸酯基(OTf)；其中，所述C6-C48的卤代芳基中的卤代表示氟代、氯代、溴代或碘代；被取代基团中的取代基为C1-C24的烷基或C1-C24烷氧基。
2.根据权利要求1所述的方法，其特征在于：所述碱性条件由下述至少一种碱提供：氢氧化锂、氢氧化钠、氢氧化钾、氢氧化钡、碳酸锂、碳酸钠、碳酸钾和碳酸铯；优选为氢氧化钠，其水溶液的质量浓度为5～25％。
3.根据权利要求1或2所述的方法，其特征在于：所述式Ⅱ所示化合物、锌及碱的投料摩尔比为1:(1～30):(1～50)，优选为1:(10～30):(10～30)。
4.根据权利要求1-3中任一项所述的方法，其特征在于：所述反应在空气或惰性气氛中进行；所述惰性气氛为氮气气氛或氩气气氛。
5.根据权利要求1-4中任一项所述的方法，其特征在于：所述反应在溶剂中进行，所述溶剂选自下述至少一种：乙腈、甲醇、乙醇、异丙醇、仲丁醇、叔丁醇、3-戊醇、2-戊醇、叔戊醇、2-甲基丁醇、3-甲基-3-戊醇、乙二醇、乙二醇单甲醚、二氯甲烷、三氯甲烷、1,4-二氧六环、苯、甲苯、二甲苯、乙酸乙酯、二甲基亚砜和四氢呋喃。
6.根据权利要求5所述的方法，其特征在于：所述溶剂为乙醇和/或异丙醇。
7.根据权利要求1-6中任一项所述的方法，其特征在于：所述反应的反应温度为25℃至回流温度，优选为70℃至回流温度；所述反应的反应时间为1～120小时，优选为48～72小时。
8.根据权利要求1-7中任一项所述的方法，其特征在于：所述式Ⅰ中，
R1、R2、R3、R4、R5、R6各自独立地表示氢、C1-C5的烷基或C1-C5的烷氧基；
R7表示C1-C5的烷基，或，取代或未取代的下述基团中的任意一种：苯基、萘基、蒽基、吡啶基、并四苯基、并五苯基、噻吩基、苯并噻吩基、硫杂蒽、硫杂并四苯、硫杂并五苯、苯并吡咯基、氮杂蒽、氮杂并四苯、氮杂并五苯；其中，被取代的基团中的取代基为C1-C24的烷基或C1-C24烷氧基。
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