Synthesis of a Hydrogenated Zigzag Carbon Nanobelt

Chen, Han; Gui, S. Z.; Zhang, Yiqun; Liu, Zhifeng; Miao, Qian

doi:10.31635/ccschem.020.202000189

Cited by 37 publications

(46 citation statements)

References 5 publications

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“…In 2020, the group of Miao reported their trial towards a benzannulated zigzag CNB (Scheme 13). [28] Iterative Diels–Alder reactions yielded macrocycle 64 . However, reduction of this macrocycle only gave a hydrogenated zigzag CNB 65 , which cannot be further oxidized to the fully conjugated zigzag CNB.…”

Section: Discussionmentioning

confidence: 99%

“…In 2020, the group of Miao reported their trial towards a benzannulated zigzag CNB (Scheme13). [28] Iterative Diels-Alder reactions yieldedm acrocycle 64.H owever,r eduction of this macrocycle only gave ah ydrogenated zigzag CNB 65,w hich cannotb ef urther oxidized to the fully conjugated zigzag CNB. This might be attributed to the high strain energy of the target CNB (124.4 kcal mol À1 )a nd instability of the target product.…”

Section: Representative Synthetic Attemptsmentioning

confidence: 98%

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Synthetic Strategies of Carbon Nanobelts and Related Belt‐Shaped Polycyclic Aromatic Hydrocarbons

Cheung

Segawa

Itami

2020

Chemistry A European J

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The developmento fc arbon nanobelts and related belt-shaped polycyclic aromatic hydrocarbons has gained momentum in recent years. This Minireview focuses on the synthetic strategies used in constructingt hese aesthetically appealing molecular nanocarbons. Examples of carbon nanobelts and relatedb elt-shaped polycyclic aromatich ydrocarbonsr eported in recent years as well as some representative synthetic attempts in earlier times are discussed.

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Section: Discussionmentioning

confidence: 99%

Section: Representative Synthetic Attemptsmentioning

confidence: 98%

Synthetic Strategies of Carbon Nanobelts and Related Belt‐Shaped Polycyclic Aromatic Hydrocarbons

Cheung

Segawa

Itami

2020

Chemistry A European J

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“…The same repetitive Diels-Alder reactions between bis(isobenzofuran) and bisbenzyne have been used very recently by Miao 51 to construct a pyrene-bearing tetraepoxyoctahydrobelt [10]arene 30. As illustrated in Scheme 7, the reaction between bisdiene 30 and bisbenzyne generated in situ from the interaction of 31 with CsF afforded a pair of syn-isomers 32 in 36% yield.…”

Section: The Stoddart Strategymentioning

confidence: 95%

Zigzag Hydrocarbon Belts

Shi

Wang

2021

CCS Chem

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Zigzag hydrocarbon belts have been fascinating chemists and materials scientists for decades because of their aesthetically appealing molecular structures, outstanding physical properties and intriguing chemical reactivities predicted by theoretical calculations, and potential applications as unique macrocyclic hosts in supramolecular chemistry. They may also serve as templates or seeds to grow structurally well-defined uniform zigzag carbon nanotubes. While there have been continuous computational studies on the structures and properties of belt[n]arenes or [n]cyclacenes since they were proposed as hypothetical molecules in 1954, the synthesis of (partially) conjugated zigzag hydrocarbon belts remains a great challenge, with no progress being reported in the past 20 years. Very recently, we have been witnessing the renaissance of synthetic interest in zigzag hydrocarbon belts, and the formation of the first fully conjugated one is on the horizon. This minireview focuses on the understanding of belt[n]arenes based on theoretical calculations and the synthesis and structure of zigzag hydrocarbon belts. Perspectives on the strategies to isolate and characterize the fully conjugated belt[n]arenes and on the applications of zigzag hydrocarbon belts are also discussed.

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“…Recently, the group of Miao reported their approach toward zigzag carbon nanobelt 25 (Scheme 3), where the C‐shaped building block, syn ‐ 30 , provides curvature and rigidity necessary for the macrocyclization. [ 31 ] The benzyne generated by treatment of bistriflate 29 with CsF was trapped by pyrenodifuran 28 resulting in the corresponding Diels‐Alder adducts, from which syn ‐ 30 was separated as a pair of regioisomers in a yield of 36%. Treatment of syn ‐ 30 with CsF triggered the next round of Diels‐Alder cycloaddition between benzyne and furan subunits leading to 31 , a tetraepoxy nanobox.…”

Section: Attempts and Success In The Synthesis Of Conjugated Nanobeltsmentioning

confidence: 99%

Recent advances and attempts in synthesis of conjugated nanobelts

Chen

Miao

2020

J of Physical Organic Chem

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Conjugated nanobelts are attractive molecules of esthetic appeal, synthetic challenges, unique properties, interesting applications, and potential impacts. The recent years have witnessed significant progress in the synthesis of carbon nanobelts and approaches to a new type of conjugated nanobelts. This review emphasizes two general synthetic strategies to approach conjugated nanobelts, and briefly covers structurally related nanobelts that are not fully conjugated, and finally provides an outlook for new directions in the field.

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Synthesis of a Hydrogenated Zigzag Carbon Nanobelt

Cited by 37 publications

References 5 publications

Synthetic Strategies of Carbon Nanobelts and Related Belt‐Shaped Polycyclic Aromatic Hydrocarbons

Synthetic Strategies of Carbon Nanobelts and Related Belt‐Shaped Polycyclic Aromatic Hydrocarbons

Zigzag Hydrocarbon Belts

Recent advances and attempts in synthesis of conjugated nanobelts

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