CN112707918B - 一种多环双酮稠环分子的制备方法 - Google Patents
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
本发明提供一种多环双酮稠环分子的制备方法，通过对反应前驱体的结构进行优化，在前驱体的酯基上引入能够能够提供空间位阻的支化烷基侧链，找到了一条更加简单制备难溶的多环(环数≧7)双酮稠环分子的方法。对于环数≧7、需要发生两次分子内傅‑克酰基化反应的多环双酮稠环分子的制备，简化了合成步骤，提高了目标产物的得率，降低了对操作环境的要求。
Description
技术领域
本发明涉及化工领域，具体是一种多环双酮稠环分子的制备方法。
背景技术
含有双酮结构的稠环单元可以直接用作有机光电材料，也可以在双酮位置进行化学修饰得到醌式结构或芴环结构单元，还可以作为结构单元构建聚合物光电材料。作为基础结构单元，含酮结构(＝O)的稠环单元的合成就显得尤为重要。如反应式I所示，芳酮结构一般通过质子酸(如浓硫酸、多聚磷酸)或路易斯酸(三氟化硼、三氯化铝)催化的傅-克反应制备，其反应前驱体多以酰氯或羧酸为主。但是，酰氯和羧酸的傅-克酰基化反应一般需要较低的反应温度，对多环反应体系(反应式II所示)的前驱体(1)或中间产物(2)的溶解性提出了较高的要求；目前文献报道的基于甲酯或乙酯(反应式II中，R＝甲氧基或乙氧基)的傅-克酰基化反应，采用路易斯酸催化的体系温度过低(-78℃)，于多环多酮稠环分子中间体溶解性不足；采用浓硫酸或三氟甲磺酸的体系腐蚀性较大；当R＝乙氧基时，反应体系升温至100℃即可溶解完全，但是体系在180℃条件下反应36h后，只能过滤得到15％的粗产物，产率较低，而且由于所含副产物或杂质较多，导致后续纯化困难。
因此，对于溶解性较差的多环(环数≧7)双酮稠环体系，亟待找到一条更加简便、安全的合成方法。
发明内容
本发明所要解决的技术问题是提供一种多环双酮稠环分子的制备方法，通过对傅-克酰基化反应的前驱体的结构进行优化，找到了一条更加简单制备难溶的多环(环数≧7)双酮稠环分子的方法。对于环数≧7、需要发生两次分子内傅-克酰基化反应的多环双酮稠环分子的制备，简化了合成步骤，降低了对操作环境的要求。
为了解决上述技术问题，本发明采用如下技术方案：多环双酮稠环分子的制备方法，步骤为：将1摩尔份反应前驱体(4)和5～7摩尔份水合对甲苯磺酸混合后溶于邻二氯苯中，氩气保护下于170～190℃条件下反应10～16h。待反应冷却至室温后，过滤反应混合物，并依次用邻二氯苯、氯仿和丙酮清洗滤饼至少2次，得到的产物用丙酮抽提10～12h，抽干得到粗产物，进一步纯化即得目标产物多环双酮稠环化合物(3)；
R1代表-H或R2代表-H或/>R1和R2只有一种是/>R1≠R2；
R3代表碳原子数大于等于8的支化烷基侧链；
Ar代表易于发生邻位取代的具有镜面对称或中心对称结构的单环芳基或稠环芳基，Ar'代表具有邻位反应活性位点的单环芳基、取代单环芳基、稠环芳基或取代稠环芳基，Ar不一定等同于Ar'，Ar的芳环环数与Ar'的芳环环数之和≥5。
优选地，R3选自异辛基、2-丁基辛基、2-辛基十二烷基或3-甲基己基；
Ar选自
Ar′选自
具体地，R1是-H，R2是R3是异辛基，Ar是/>Ar′是或R1是/>R2是-H，R3是异辛基，Ar是/>Ar′是/>
实验结果证明，仅通过在反应前驱体上引入能够提供空间位阻的支化烷基侧链(R3)的酯基，就能直接且高效的完成分子内傅-克酰基化反应，得到难溶的多环双酮稠环分子。该合成方法与文献报道相比，简化了合成步骤，提高了目标产物的得率。且引入的含支化位点的酯基侧链解决了中间产物难溶的问题，因此该方法可以用于合成环数更多(环数≧7)的双酮稠环分子。
本发明的多环双酮稠环分子的制备方法，通过向酯基中引入大空间位阻官能团R3，代替目前常用的甲基或乙基，提高反应前驱体和半反应中间产物的溶解性，从而提高目标产物的产率。而且通过支化侧链取代的芳香酯直接进行傅-克酰基化反应，省略了酯皂化反应成酸再转化成酰氯的步骤，同时提供了一条可用于合成难溶多环(环数≧7)双酮稠环分子的有效方法。该类芳香酮产物可直接用作有机薄膜晶体管材料，也可以通过进一步化学修饰用于构建其他有机光电材料。
附图说明
图1是反应前驱体(5)的红外吸收光谱谱图。
图2是目标产物(6)的红外吸收光谱谱图。
图3是目标产物(6)的核磁共振氢谱谱图。
图4是产物(9)的核磁共振氢谱谱图。
具体实施方式
下面结合实施例对本发明作进一步描述：
实施例1：R1＝-H，R3＝—CH2CH(CH2CH3)CH2CH2CH2CH3(异辛基)，
将反应前驱体(5)(537.7mg，0.82mmol)和水合对甲苯磺酸(780mg，4.1mmol)混合后溶于180mL邻二氯苯中，氩气保护下于180℃条件下反应12h。待反应冷却至室温后，过滤反应混合物，并依次用邻二氯苯、氯仿和丙酮清洗滤饼2次，得到的产物用丙酮抽提10h，抽干得到285mg褐色粗产物(Y＝88％)。该粗产物进一步通过真空升华装置提纯，收集到135-145℃阶段的墨绿色产物213mg，即为目标产物七环双酮稠环分子(6)产率为66％。将2mg/mL的目标产物(6)溶于氘代乙烷中进行高温1H NMR测试(目标产物的溶解度太低，难以计算耦合常数)。1H NMR(400MHz,C2D2Cl4,δ):8.184(d,2H),7.878(s,2H),7.527～7.330(m,6H)。
从红外吸收光谱(图1、图2)可以看出：酮羰基的伸缩振动峰在1699.17cm-1，酯羰基/>的伸缩振动峰在1724.28cm-1；且酯基在1400-1000cm-1指纹区吸收峰明显，主要包含饱和C-H键的弯曲振动，C-O键的伸缩振动，C-C单键的骨架振动等峰值，而目标分子(6)在该区域吸收较弱，从而确定分子结构。
实验过程中发现该前驱体(5)在对甲苯磺酸催化下进行反应时，体系升温至50℃即溶解完全，且经过180℃条件下反应12h后，得到了褐色粗产物(后经真空升华提纯，证实了产物的结构)。后又尝试降低反应体系的温度，发现当降至160℃，反应时间延长至36h，但是不溶的粗产品产率却降到了37％。由此推测：引入异辛基(R3)提高了反应中间体的溶解度。
实施例2：R2＝-H，R3＝—CH2CH(CH2CH3)CH2CH2CH2CH3(异辛基)，
前驱体(7)(612.8mg，1mmol)和水合对甲苯磺酸(951.2mg，5mmol)混合后溶于20mL邻二氯苯中，氩气保护下于180℃反应12h。待反应冷却后，过滤反应混合物，依次用邻二氯苯、氯仿和丙酮清洗滤饼2次，得到的产物用丙酮抽提10h，抽干得到323.5mg深褐色的粗产物(8)(Y＝82％)。
将该粗产物(8)分散于50mL干燥的四氢呋喃中，缓慢滴入反应好的19mL三异丙基硅基锂(TIPS-Li 1.9mmol)的四氢呋喃溶液中，保持-78℃反应2h。反应体系自然升至室温后，加入1mL去离子水，继续反应10min。将反应液倾倒至300mL水中，用150mL二氯甲烷萃取3次，饱和食盐水洗涤三次后经无水硫酸镁干燥，旋转蒸发除掉溶剂，真空抽干得到紫黑色粗产物566.8mg。以二氯甲烷为洗脱剂，快速柱分离后，经重结晶(四氢呋喃：石油醚＝1:1)得到480mg紫红色产物(9)，两步反应总产率约61％。1H NMR(400MHz,CHCl3,δ):7.352(t,2H),7.256(m,4H),7.131(m,4H)，1.201-1.384(m,96H)。
(注：紫红色产物(9)在酸性和中性液相色谱柱分离过程中会变质，可能影响最终反应产率；且紫红色产物(9)的氯仿溶液在室温放置一天后明显褪色，这一现象也进一步确认了产物的结构(这种醌式结构稳定性较差)。
Claims (1)
1.一种多环双酮稠环分子的制备方法，其特征在于，其步骤为：
将1摩尔份反应前驱体(4)和5～7摩尔份水合对甲苯磺酸混合后溶于邻二氯苯中，氩气保护下于170～190℃条件下反应10～16h,待反应冷却至室温后，过滤反应混合物，并依次用邻二氯苯、氯仿和丙酮清洗滤饼至少2次，得到的产物用丙酮抽提10～12h，抽干得到粗产物，进一步纯化即得目标产物多环双酮稠环化合物(3)；
式中：R1是-H，R2是R3是异辛基，Ar是/>Ar′是/>
或
R1是R2是-H，R3是异辛基，Ar是/>Ar′是/>
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