通过Scholl反应合成螺烯类纳米碳分子的研究进展

doi:10.6023/cjoc202107063

摘要/Abstract

近年来, 通过有机合成方式构建的结构精确的纳米碳材料备受关注, 展现出独特的性质和广阔的应用前景. 将具有螺旋手性的螺烯与大尺寸的分子基纳米碳结合, 产生了一类独特的手性纳米碳分子, 在手性光学、手性光电子学及自旋电子学等领域具有潜在的应用价值. 然而, 由于其特殊的螺旋结构及分子内较大的张力, 这类纳米碳分子的合成颇具挑战. 在合成螺烯类纳米碳分子的几类常用方法中, Scholl反应条件温和且十分高效, 被广泛使用. 从合成的角度出发, 详细综述了通过Scholl反应构建螺烯类纳米碳分子的研究进展, 并对该领域未来的发展提出展望.

关键词: 螺烯, 纳米碳分子, 手性材料, 手性纳米碳, Scholl反应, 关环反应

Molecular nanocarbon materials with well-defined structures constructed through organic synthesis have attracted much attention in recent years, exhibiting unique properties and broad applications in many areas. The combination of helicenes and molcular nanocarbons generates a fancinating type of chiral molecular nanocarbons with potential applications in the fields of chiral optics, chiral optoelectronics and spintronics etc. However, it is of greart challenge to synthesize these molecules due to the large intramolecular strain and the special helical structure. Among various synthetic strategies, the Scholl reaction possesses the advantages of mild conditions and high efficiency. In this review, recent advances in the syntheses of helicene-based molecular nanocarbons via the Scholl reaction are summarized, and our perspectives to stimulate further development of the chiral nanocarbon materials are also provided.

Key words: helicene, molecular nanocarbon, chiral materials, chiral nanocarbon, Scholl reaction, cyclization reaction

引用此文

陈星宇, 李继坤, 王小野. 通过Scholl反应合成螺烯类纳米碳分子的研究进展[J]. 有机化学, 2021, 41(11): 4105-4137.

Xing-Yu Chen, Ji-Kun Li, Xiao-Ye Wang. Recent Advances in the Syntheses of Helicene-Based Molecular Nanocarbons via the Scholl Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4105-4137.

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图/表 34

图式1. 肖尔反应示例及可能的机理

Scheme 1. An example of the Scholl reaction and the possible mechanisms

图式2. 含单螺烯的双层纳米碳分子的合成

Scheme 2. Synthesis of helical bilayer nanographene

图式3. π拓展的单螺烯9、11和13的合成

Scheme 3. Synthesis of π-extended monohelicenes 9, 11 and 13

图式4. 单螺烯类纳米碳分子17和19的合成

Scheme 4. Synthesis of monohelicene-based nanocarbons 17 and 19

图式5. 含七元环的单螺烯类纳米碳分子21的合成

Scheme 5. Synthesis of monohelicene-based nanocarbon 21 with a seven-membered ring

图式6. 含七元环的单螺烯类纳米碳分子27的合成

Scheme 6. Synthesis of monohelicene-based nanocarbon 27 with seven-membered rings

图式7. 含八元环的单螺烯类纳米碳分子的合成

Scheme 7. Synthesis of monohelicene-based nanocarbons with eight-membered rings

图式8. 含九元环的单螺烯类纳米碳分子的合成

Scheme 8. Synthesis of monohelicene-based nanocarbons with nine-membered rings

图式9. 含五元环的单螺烯类纳米碳分子38和40的合成

Scheme 9. Synthesis of monohelicene-based nanocarbons 38 and 40 with five-membered rings

图式10. 含五元环的单螺烯类纳米碳分子42的合成

Scheme 10. Synthesis of monohelicene-based nanocarbons 42 with five-membered rings

图式11. 双[5]螺烯纳米碳分子46和48的合成及衍生物49的分子结构

Scheme 11. Synthesis of molecular nanocarbons 46 and 48 containing double [5]helicene, as well as the molecular structures of their derivatives 49

图式12. 双[5]螺烯纳米碳分子的合成

Scheme 12. Synthesis of molecular nanocarbons containing double [5]helicene

图式13. 双[6]螺烯纳米碳分子59、63和硫杂螺烯类纳米碳分子66、68的合成

Scheme 13. Synthesis of double [6]helicene-based nanocarbons 59, 63 and thiophene-fused nanocarbons 66, 68

图式14. 单[7]螺烯和双[7]螺烯类纳米碳分子71和74的合成

Scheme 14. Synthesis of mono and double [7]helicene-based nanocarbons 71, 74

图式15. 硼氮杂双螺烯77和79的合成

Scheme 15. Synthesis of BN-embedded double helicenes 77 and 79

图式16. 基于HBC的双螺烯81和83的合成

Scheme 16. Synthesis of HBC-based double helicenes 81 and 83

图式17. 双[7]螺烯86及其衍生物的合成

Scheme 17. Synthesis of double [7]helicene 86 and its derivatives

图式18. 含心环烯结构的双螺烯94、96和98的合成

Scheme 18. Synthesis of corannulene-based double helicenes 94, 96 and 98

图式19. 多重螺烯100和105的合成

Scheme 19. Synthesis of multiple helicenes 100 and 105

图式20. 以rubicene为核的多重螺烯的合成

Scheme 20. Synthesis of multiple helicenes based on the rubicene core

图式21. 六重[7]螺烯和[9]螺烯的合成(为清晰起见, 分子112, 115和118的取代基已省略)

Scheme 21. Synthesis of hexapole [7]helicene and hexapole [9]helicene (the substituents on compounds 112, 115 and 118 are omitted for clarity)

图式22. 含有七元环及八元环的多重螺烯的合成

Scheme 22. Synthesis of multiple helicenes containing seven- and eight-membered rings

图式23. 螺旋碳纳米带129的合成

Scheme 23. Synthesis of ribbon-shaped helical nanocarbons 129

图式24. 含七元环的螺旋碳纳米带137和138的合成

Scheme 24. Synthesis of ribbon-shaped helical nanocarbons 137 and 138 with seven-membered rings

图式25. 非平面的碳纳米带145的合成

Scheme 25. Synthesis of nonplanar carbon nanoribbon 145

图式26. 重排反应合成螺烯类纳米碳分子149及机理

Scheme 26. Synthesis of helicene-based nanocarbons 149 via the rearrangement reaction and its mechanism

图式27. 利用重排反应合成螺烯类纳米碳分子152和153

Scheme 27. Synthesis of helicene-based nanocarbons 152 and 153 via the rearrangement reaction

图式28. 形成分子152的重排反应机理

Scheme 28. The rearrangement mechanism of forming 152

图式29. 分子156的可能关环方式

Scheme 29. Potential ring-closing pathways of 156

图式30. 分子156的重排反应机理

Scheme 30. Rearrangement mechanism of 156

图式31. 分子160的可能关环方式及重排反应式

Scheme 31. Potential ring-closing pathway and the rearrangement reaction of 160

图式32. 分子160的重排反应机理

Scheme 32. Rearrangement mechanism of 160

图式33. 螺烯的重排反应及机理

Scheme 33. Rearrangement reaction of helicenes and its mechanism

图式34. 分子174~177的重排反应式

Scheme 34. Rearrangement reactions of compounds 174~177

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