N-doped nonalternant aromatic belt <i>via</i> a six-fold annulative double N-arylation

Sato, Hiroki; Suizu, Rie; Kato, Tomoki; Yagi, Akiko; Segawa, Y.; Awaga, Kunio; Itami, Kenichiro

doi:10.1039/d2sc02647c

Cited by 17 publications

(11 citation statements)

References 40 publications

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“…Since this report, fascinating properties of infinitene have been predicted. − Wu and Isobe et al synthesized a twisted CNB in 2021 and a fused [5]helicene dimer in 2023 , as a related molecule of infinitene. In addition to aromatic hydrocarbon-based CNBs, heteroatom-embedded CNBs have also been reported. − In 2019, Tanaka et al synthesized the first oxygen-embedded CNB by rhodium-catalyzed alkyne cyclotrimerization . Since then, CNBs with various topologies such as the armchair, zigzag, and Möbius-type CNBs, have been synthesized through the strategy developed by Tanaka’s group. − Nitrogen-embedded CNBs have also been synthesized by our group, Wu et al, and Chen et al − These heteroatom-containing nanobelts are also one of emerging molecules because of their unique properties derived from synergies between nanobelts and heteroatoms .…”

Section: Synthesis Of Cnbs and Related Aromatic Beltsmentioning

confidence: 99%

Carbon Nanobelts: Brief History and Perspective

Imoto,

Yagi,

Itami

2023

Precision Chemistry

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Carbon nanotubes (CNTs) are an emerging nanomaterial because of their outstanding performance in various applications. In recent years, the segment molecules of CNTs, referred to as carbon nanorings (CNRs) or carbon nanobelts (CNBs), have gained attention for their unique structures and properties, as well as their potential as seed molecules for the precise synthesis of CNTs. CNBs are rigid and thick segments of CNTs whose synthesis has been addressed by scientists fascinated by the uniqueness of CNBs long before the discovery of CNTs. After 60 years of efforts by synthetic chemists all over the world, the synthesis of the first CNB, (6,6)CNB, was achieved by our group in 2017. Since this milestone, diverse types of nanobelts have been synthesized through various synthetic routes, thereby demonstrating their photophysical, magnetic, and redox properties derived from rigid belt structures. The applications of CNBs have also been introduced recently. The formation of the host–guest complex, transformation to three-dimensional molecules, and measurement of conductivity have been reported for CNBs. This paper summarizes the brief history and perspective of CNBs. Further synthetic campaigns and aggressive application of CNBs would create novel and groundbreaking scenes in materials science.

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Section: Synthesis Of Cnbs and Related Aromatic Beltsmentioning

confidence: 99%

Carbon Nanobelts: Brief History and Perspective

Imoto,

Yagi,

Itami

2023

Precision Chemistry

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“…These belt compounds have been shown to adopt unique structures and exhibit interesting molecular recognition properties. [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] We reported previously a synthetic strategy to synthesize zigzag hydrocarbon belts by stitching all fjords of resorcin-[n]arene derivatives through multiple intramolecular alkylation [9,10] and acylation [11] reactions. The strategy has been applied successfully in the construction of various belt structures including heteroatom-and cycloheptatriene-embedded belts.…”

Section: Introductionmentioning

confidence: 99%

“…Very recently, Wu [33] disclosed the construction of [1,5]diazocine‐incorporated zigzag belts. These belt compounds have been shown to adopt unique structures and exhibit interesting molecular recognition properties [17–33] …”

Section: Introductionmentioning

confidence: 99%

“…[9,[13][14][15] These breakthroughs have initiated a resurgence of the research area. [1-4-16] One of the noteworthy endeavors is the exploration of belt structures which contain other carbocyclic [17][18][19][20] and heterocyclic rings [21][22][23][24][25][26][27][28][29][30][31] in addition to hexagonal benzene rings. For instance, multiple intramolecular ring closure metathesis reactions of vinyl-substituted resorcin[n]arene derivatives have been reported to produce cycloheptatrieneembedded belts (type B in Figure 1) [17] while per-triflated pillarene derivatives and analogs have been found to undergo Yamamoto coupling reaction to afford cyclopentadienedoped belt compounds (type C in Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Functionalized Hydrocarbon Belts: Synthesis, Structure and Properties

Tong

Zhang

et al. 2023

Angew Chem Int Ed

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Hydrocarbon belts have drawn great attention because of their unique structures and tantalizing properties. Although a few belts and heteroatom-doped analogs have been synthesized, belt molecules containing non-hexagonal rings remain rare. Herein we report the construction and application of unprecedented zigzag-type hydrocarbon belts which contain functionalized eight-membered rings. The synthesis features fourfold intramolecular acylation reactions of resorcin-[4]arene-derived intermediates, which affords C 4symmetric tetrabenzobelt[4]arene[4]cyclooctatrienones. Stereoselective ketone reduction with LiAlH 4 and nucleophilic addition with alkynyllithiums provide the corresponding tetrahydroxylated belts. The tetraol and its methyl ether are powerful and selective hosts to form 2 : 1 and 1 : 1 complexes with cesium ion, respectively, with binding constants up to (1.71 � 0.33) × 10 11 M À 2 and (1.50 � 0.16) × 10 6 M À 1 . In addition, enantiopure C 4 -symmetric belts can emit CPL with j g lum j being around 0.01.

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“…2 b ,5 The incorporation of main group heteroatoms (such as B, N, and S) has proved an efficient strategy to build π-conjugated materials with unique optoelectronic properties. 6 Such a group of heteroatom-doped macrocycles are expected to show distinct electronic structures compared with all-carbon based analogues, and their frontier molecular orbitals can be tuned.…”

Section: Introductionmentioning

confidence: 99%