Recent Advances in the Syntheses of Helicene-Based Molecular Nanocarbons via the Scholl Reaction

doi:10.6023/cjoc202107063

Abstract

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

Cite this article

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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Fig. & Tab. 34

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

Scheme 2. Synthesis of helical bilayer nanographene

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 19. Synthesis of multiple helicenes 100 and 105

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

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

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

Scheme 23. Synthesis of ribbon-shaped helical nanocarbons 129

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

Scheme 25. Synthesis of nonplanar carbon nanoribbon 145

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

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

Scheme 28. The rearrangement mechanism of forming 152

Scheme 29. Potential ring-closing pathways of 156

Scheme 30. Rearrangement mechanism of 156

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

Scheme 32. Rearrangement mechanism of 160

Scheme 33. Rearrangement reaction of helicenes and its mechanism

Scheme 34. Rearrangement reactions of compounds 174~177

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通过Scholl反应合成螺烯类纳米碳分子的研究进展