CN112480050B - 一种富勒烯并螺环衍生物的合成方法 - Google Patents
一种富勒烯并螺环衍生物的合成方法 Download PDFInfo
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Abstract
本发明公开了一种富勒烯并螺环衍生物的合成方法,属于富勒烯衍生物的合成技术领域。本发明的技术方案要点为:以邻碘苯酚/邻碘苯胺的含端烯类化合物为反应原料,在钯盐Pd(PPh3)4催化和铯盐Cs2CO3促进作用下,与富勒烯C60于130‑150℃反应经Heck/C‑H活化的串联过程,同时形成三个C‑C键并构筑两个环,一锅法直接合成结构多样化的富勒烯并螺环衍生物。本发明生产工艺简单,环境友好,底物适用范围广,具有较高的产率;并且本生产工艺使用的过渡金属催化的多米诺策略不仅适于螺环结构的合成,而且也适于其它复杂富勒烯衍生物结构的合成。
Description
技术领域
本发明属于富勒烯衍生物的合成技术领域,具体涉及一种富勒烯并螺环衍生物的合成方法。
背景技术
富勒烯C60具有三维的大π电子体系,因此具有良好的接受电子性能及较高的电子迁移率,是一种良好的n-型半导体材料。富勒烯衍生物是一类在光电转移材料和太阳能电池受体材料等领域具有广泛和重要应用的碳纳米分子。由于结构与光电性质密切相关,发展新的方法构建具有多样化结构特征的富勒烯衍生物具有重要的意义。在众多已知的富勒烯衍生物中,富勒烯并螺环结构较少且制备方法有限。因此,发展新的方法制备富勒烯螺环衍生物是亟需解决的问题。本发明设计了钯催化的多米诺螺环化反应,并且使用易获取的原料,经Heck/C-H活化的串联过程,同时形成三个C-C键并构筑两个环,一锅法直接制备了结构多样化的富勒烯并螺环衍生物。
发明内容
本发明解决的技术问题是提供了一种工艺简单、环境友好、底物适用范围广且具有较高产率的富勒烯并螺环衍生物的合成方法,该方法以邻碘苯酚/邻碘苯胺的含端烯类化合物为反应原料,在钯盐的催化作用下,与富勒烯C60反应经Heck/C-H活化的串联过程,同时形成三个C-C键并构筑两个环,一锅法直接合成结构多样化的富勒烯并螺环衍生物。
本发明为解决上述技术问题采用如下技术方案,一种富勒烯并螺环衍生物的合成方法,其特征在于具体过程为:以邻碘苯酚/邻碘苯胺的含端烯类化合物为反应原料,在钯盐Pd(PPh3)4催化和铯盐Cs2CO3促进作用下,与富勒烯C60于130-150℃反应经Heck/C-H活化的串联过程,同时形成三个C-C键并构筑两个环,一锅法直接合成结构多样化的富勒烯并螺环衍生物,该合成过程中的反应方程式为:
其中R=H或Bn;R1=H、MeO、Br或CO2Me;R2=H、MeO、F、Cl或CF3。
进一步优选,所述富勒烯并螺环衍生物的合成方法,其特征在于具体步骤为:取干燥的反应管依次加入富勒烯C60、邻碘苯酚/邻碘苯胺的含端烯类化合物、钯盐Pd(PPh3)4和铯盐Cs2CO3,超声将固体分散在无水CB中,将反应管置于130-150℃的油浴中反应24-48h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用CS2/DCM为洗脱剂得到目标产物富勒烯并螺环衍生物。
进一步优选,所述富勒烯C60、邻碘苯酚/邻苯苯胺的含端烯类化合物与钯盐Pd(PPh3)4的投料摩尔比为1:2:0.05。
本发明具有以下有益效果:本发明生产工艺简单,环境友好,底物适用范围广,具有较高的产率;并且本生产工艺使用的过渡金属催化的多米诺策略不仅适于螺环结构的合成,而且也适于其它复杂富勒烯衍生物结构的合成。
具体实施方式
以下通过实施例对本发明的上述内容做进一步详细说明,但不应该将此理解为本发明上述主题的范围仅限于以下的实施例,凡基于本发明上述内容实现的技术均属于本发明的范围。
实施例1
富勒烯并螺环衍生物2a的制备
反应步骤:
取一个干燥的15mL史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物(0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于130℃的油浴中反应24h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用体积比CS2/DCM=8:1为洗脱剂得到目标产物富勒烯并螺环衍生物2a,产物2a的分离产率是48%。
产物2a:1H NMR(400MHz,CDCl3/CS2)δ7.77(d,J=7.6Hz,1H),7.69(d,J=7.2Hz,1H),7.57–7.49(m,2H),7.37(d,J=7.6Hz,1H),7.23(t,J=8.0Hz,1H),6.91(t,J=8.0Hz,2H),6.63(d,J=9.2Hz,1H),5.02(d,J=9.2Hz,1H),4.85(d,J=15.2Hz,1H),4.55(d,J=14.8Hz,1H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3as relaxation reagent)δ161.7,158.2,157.4,152.9,152.4,148.0,147.5,147.4,146.5,146.4,146.35,16.3,146.15,146.1,146.07,145.9,145.7,145.6,145.4,145.37,145.3,145.2,145.1,145.0,144.9,144.5,144.43,144.4,144.37,144.2,142.9,142.8,142.5,142.47,142.44,142.4,142.2,142.1,142.05,142.0,141.9,141.88,141.6,141.5,141.3,141.28,140.9,140.15,140.1,138.7,137.0,136.1,136.0,135.8,135.1,134.9,130.8,130.2,129.0,128.5,128.0,127.1,125.3,119.4,110.5,81.1,73.3,65.2,62.4,45.8;FT-IRν/cm-1 2934,1592,1481,1460,1221,1099,1024,1002,845,751,696,575,552,526;UV-vis(CHCl3)λmax/nm258,312,433,699;MALDI-TOF MS m/z calcd for C75H12O[M]-928.0894,found 928.0888。
实施例2
富勒烯并螺环衍生物2b的制备
反应步骤:
取一个干燥的15mL史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物(0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于130℃的油浴中反应24h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用体积比CS2/DCM=8:1为洗脱剂得到目标产物富勒烯并螺环衍生物2b,产物2b的分离产率是40%。
产物2b:1H NMR(600MHz,CDCl3/CS2)δ7.83(d,J=7.8Hz,1H),7.69(d,J=7.2Hz,1H),7.56(t,J=7.8Hz,1H),7.53(t,J=7.8Hz,1H),6.92(s,1H),6.81–6.78(m,2H),6.60(d,J=9.0Hz,1H),5.01(d,J=9.0Hz,1H),4.85(d,J=15.0Hz,1H),4.55(d,J=15.0Hz,1H),3.65(s,3H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3as relaxation reagent)δ158.3,157.4,156.2,153.1,152.7,152.5,148.1,147.5,147.4,146.6,146.45,146.4,146.36,146.2,146.17,146.1,145.9,145.7,145.6,145.57,145.5,145.4,145.37,145.2,145.1,145.07,145.0,144.6,144.5,144.44,144.42,144.3,143.0,142.9,142.6,142.5,142.48,142.2,142.12,142.1,142.0,141.9,141.87,141.7,141.6,141.4,141.37,141.0,140.22,140.2,138.7,136.9,136.2,135.9,135.8,135.1,135.0,129.1,128.6,128.1,127.1,126.1,116.4,116.3,110.6,81.4,73.2,65.3,62.9,55.9,45.8;FT-IRν/cm-1 2923,1709,1511,1486,1423,1354,1263,1197,1031,1004,865,805,753,696,575,552,524;UV-vis(CHCl3)λmax/nm 252,312,432,701;MALDI-TOF MS m/z calcd for C76H14O2[M]-958.0999,found 958.0995。
实施例3
富勒烯并螺环衍生物2c的制备
反应步骤:
取一个干燥的15mL史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物(0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于130℃的油浴中反应24h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用体积比CS2/DCM=8:1为洗脱剂得到目标产物富勒烯并螺环衍生物2c,产物2c的分离产率是45%。
产物2c:1H NMR(600MHz,CDCl3/CS2)δ7.72(d,J=7.2Hz,1H),7.68(d,J=6.6Hz,1H),7.58–7.53(m,2H),7.44(s,1H),7.31(d,J=8.4Hz,1H),6.78(d,J=8.4Hz,1H),6.63(d,J=9.6Hz,1H),5.04(d,J=9.0Hz,1H),4.80(d,J=14.4Hz,1H),4.55(d,J=15.0Hz,1H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3as relaxation reagent)δ160.9,157.8,156.9,152.4,151.5,147.4,147.3,146.4,146.3,146.1,146.0,145.8,145.5,145.45,145.3,145.28,145.2,145.1,144.9,144.8,144.4,144.3,144.26,142.83,142.8,142.5,142.4,142.38,142.35,142.1,142.0,141.8,141.6,141.4,141.2,138.7,137.0,136.2,136.0,135.6,134.9,134.7,133.2,132.9,129.1,128.7,128.2,127.8,126.7,111.9,111.4,81.6,73.0,65.0,62.3,45.7;FT-IRν/cm-1 1708,1460,1261,1219,1201,1102,1000,964,899,868,797,757,697,676,574,550,526;UV-vis(CHCl3)λmax/nm 255,313,461,696;MALDI-TOF MS m/z calcd for C74H11BrO[M]-1005.9999,found 1005.9991。
实施例4
富勒烯并螺环衍生物2d的制备
反应步骤:
取一个干燥的15mL史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物(0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于140℃的油浴中反应24h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用体积比CS2/DCM=8:1为洗脱剂得到目标产物富勒烯并螺环衍生物2d,产物2d的分离产率是32%。
产物2d:1H NMR(400MHz,CDCl3/CS2)δ8.04(s,1H),7.96(dd,J=8.4,1.6Hz,1H),7.68(t,J=6.8Hz,2H),7.59–7.51(m,2H),6.91(d,J=8.4Hz,1H),6.71(d,J=9.2Hz,1H),5.11(d,J=9.2Hz,1H),4.81(d,J=14.8Hz,1H),4.57(d,J=14.8Hz,1H),3.79(s,3H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3as relaxation reagent)δ166.1,165.9,158.1,157.2,152.6,151.8,147.7,147.63,147.6,146.7,146.6,146.57,146.4,146.3,146.28,146.1,145.8,145.77,145.75,145.6,145.59,145.51,145.5,145.47,145.4,145.36,145.2,145.1,144.8,144.64,144.6,144.5,144.2,143.1,143.06,142.8,142.7,142.62,142.6,142.3,142.28,142.2,142.1,141.9,141.65,141.63,141.6,141.5,141.4,141.1,140.4,140.37,138.9,137.4,136.5,136.4,135.9,135.3,135.0,129.3,128.9,128.4,127.1,126.1,122.0,110.4,82.5,73.4,65.4,62.1,51.9,46.1;FT-IRν/cm-1 1712,1607,1510,1437,1286,1229,1114,1019,996,797,761,733,698,676,574,552,525;UV-vis(CHCl3)λmax/nm 257,312,434,699;MALDI-TOF MS m/z calcd for C77H14O3[M]-986.0948,found 986.0942。
实施例5
富勒烯并螺环衍生物2e的制备
反应步骤:
取一个干燥的15mL史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物(0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于130℃的油浴中反应24h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用体积比CS2/DCM=8:1为洗脱剂得到目标产物富勒烯并螺环衍生物2e,产物2e的分离产率是40%。
产物2e:1H NMR(400MHz,CDCl3/CS2)δ7.67(d,J=8.8Hz,1H),7.35(d,J=7.6Hz,1H),7.22(m,2H),7.00(dd,J=8.4,2.8Hz,1H),6.90(t,J=8.0Hz,2H),6.60(d,J=9.2Hz,1H),4.98(d,J=9.2Hz,1H),4.84(d,J=14.8Hz,1H),4.49(d,J=14.8Hz,1H),3.95(s,3H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3as relaxation reagent)δ162.0,159.7,158.3,157.5,153.2,152.8,148.2,147.6,147.57,146.7,146.6,146.5,146.3,146.27,146.2,146.0,145.9,145.8,145.78,145.5,145.46,145.3,145.27,145.2,145.1,144.7,144.6,144.5,144.4,143.1,143.0,142.7,142.63,142.6,142.58,142.3,142.25,142.2,142.17,142.0,141.8,141.6,141.5,141.49,141.45,141.1,140.3,138.8,137.3,137.2,136.2,136.17,135.4,135.1,134.2,130.8,130.2,128.6,125.8,119.5,114.9,112.8,110.7,81.6,73.6,65.4,62.1,55.3,46.2;FT-IRν/cm-12829,1607,1591,1495,1478,1458,1422,1315,1251,1215,1158,1097,1024,900,813,751,725,575,551,525;UV-vis(CHCl3)λmax/nm 258,312,434,721;MALDI-TOF MS m/z calcd for C76H14O2[M]-958.0999,found958.0994。
实施例6
富勒烯并螺环衍生物2f的制备
反应步骤:
取一个干燥的15mL史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物(0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于150℃的油浴中反应24h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用体积比CS2/DCM=8:1为洗脱剂得到目标产物富勒烯并螺环衍生物2f,产物2f的分离产率是30%。
产物2f:1H NMR(400MHz,CDCl3/CS2)δ7.75(dd,J=8.8,5.2Hz,1H),7.41(dd,J=8.4,2.4Hz,1H),7.34(d,J=7.6Hz,1H),7.23(t,J=7.6Hz,1H),7.18(td,J=8.4,2.4Hz,1H),6.92–6.87(m,2H),6.60(d,J=9.2Hz,1H),4.98(d,J=9.2Hz,1H),4.83(d,J=14.8Hz,1H),4.53(d,J=15.2Hz,1H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3asrelaxation reagent)δ163.3,161.9,161.6,157.7,156.9,152.6,152.2,147.9,147.5,147.4,146.5,146.45,146.4,146.2,146.15,146.1,145.9,145.7,145.6,145.5,145.44,145.4,145.3,145.2,145.14,145.1,144.8,144.5,144.4,144.37,144.0,143.0,142.9,142.6,142.5,142.49,142.46,142.2,142.1,142.0,141.96,141.9,141.7,141.5,141.34,141.3,141.29,141.0,140.2,140.18,138.7,138.2,138.1,137.8,137.1,136.1,135.9,135.1,135.0,130.5,130.4,129.2,129.1,125.2,119.6,116.2,116.0,114.6,114.5,110.7,81.1,73.2,65.0,62.0,45.7;FT-IRν/cm-1 2918,1710,1597,1479,1454,1427,1247,1197,1147,1096,1024,1003,862,819,750,696,574,551,525;UV-vis(CHCl3)λmax/nm 256,313,433,700;MALDI-TOF MS m/z calcd for C75H11FO[M]-946.0799,found 946.0795。
实施例7
富勒烯并螺环衍生物2g的制备
反应步骤:
取一个干燥的15mL的史莱克管,依次向其中加入富勒烯C60(36.0mg,0.05mmol),化合物0.1mmol),Pd(PPh3)4(2.9mg,0.0025mmol)和Cs2CO3(32.6mg,0.1mmol),超声将固体溶解在无水CB(6mL)中,将反应管置于130℃的油浴中反应48h,反应结束后将反应管提起冷却至室温,装一根短硅胶柱用CS2/CH2Cl2为洗脱剂滤去金属盐及不溶物,减压旋出溶剂。接着用较少的CS2将样品溶解采用薄层层析硅胶柱分离,进行湿法上样,先用CS2为洗脱剂回收未反应的富勒烯C60,再用体积比CS2/CH2Cl2=5:1为洗脱剂得到目标化合物2g,产物2g的分离产率是40%。
产物2g:1H NMR(400MHz,CDCl3/CS2)δ7.72(d,J=8.4Hz,1H),7.69(d,J=2.0Hz,1H),7.47(dd,J=8.4,2.0Hz,1H),7.34(d,J=7.2Hz,1H),7.24(t,J=8.0Hz,1H),6.93–6.88(m,2H),6.60(d,J=9.2Hz,1H),4.98(d,J=9.2Hz,1H),4.81(d,J=15.2Hz,1H),4.52(d,J=14.8Hz,1H);13C{1H}NMR(150MHz,CDCl3/CS2 with Cr(acac)3as relaxationreagent)δ162.0,157.8,157.0,152.7,152.2,147.9,147.6,147.5,146.6,146.5,146.49,146.48,146.3,146.24,146.2,146.0,145.8,145.7,145.6,145.53,145.5,145.4,145.3,145.2,145.18,144.9,144.6,144.5,144.49,144.4,144.1,143.0,142.96,142.7,142.6,142.58,142.5,142.3,142.2,142.1,142.09,142.07,142.0,141.8,141.6,141.4,141.38,141.0,140.6,140.3,140.26,138.8,137.9,137.1,136.2,136.0,135.2,135.0,134.5,130.6,130.5,129.1,128.8,128.1,125.1,119.7,110.7,81.0,73.7,65.0,62.2,45.5;FT-IRν/cm-1 2973,2879,1592,1510,1478,1450,1379,1318,1087,1046,879,821,795,744,573,551,525;UV-vis(CHCl3)λmax/nm 260,314,434,698;MALDI-TOF MS m/z calcd forC75H11ClO[M]-962.0504,found 962.0500。
以上实施例描述了本发明的基本原理、主要特征及优点,本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明原理的范围下,本发明还会有各种变化和改进,这些变化和改进均落入本发明保护的范围内。
Claims (5)
2.根据权利要求1所述的富勒烯并螺环衍生物的合成方法,其特征在于具体步骤为:取干燥的反应管依次加入富勒烯C60、邻碘苯酚/邻碘苯胺的含端烯类化合物、钯盐Pd(PPh3)4和铯盐Cs2CO3,超声将固体分散在无水CB中,将反应管置于130-150℃的油浴中反应24-48h,反应结束后将反应管提起冷却至室温,真空蒸发溶剂后将残留物在硅胶柱上进行分离,以CS2为洗脱剂,以回收未反应的富勒烯C60,再用CS2/DCM为洗脱剂得到目标产物富勒烯并螺环衍生物。
3.根据权利要求1或2所述的富勒烯并螺环衍生物的合成方法,其特征在于:所述富勒烯C60、邻碘苯酚/邻苯苯胺的含端烯类化合物与钯盐Pd(PPh3)4的投料摩尔比为1:2:0.05。
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