Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons

Ito, Shingo; Tokimaru, Yuki; Nozaki, Kyoko

doi:10.1039/c4cc06643j

Cited by 73 publications

(80 citation statements)

References 43 publications

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“…151 With 61 as the basic unit, its dimer 62 was also successfully synthesized, suggesting the possibility of further lateral extension toward N-doped zigzag-edge GNRs. 153 Furthermore, generation of 61 at a high temperature provided self-dimerization product 63 in 51% yield, which might serve as a precursor for an unprecedented p-HBC with two nitrogen atoms inside the aromatic core. Azomethine ylide 61 could be employed in 1,3-dipolar cycloaddition reactions with various dipolarophiles, providing a unique pathway to N-doped PAHs with fused pyrrole rings.…”

Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting renewed and more widespread attention since the first experimental demonstration of graphene in 2004. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. The precise synthesis of quasi-zero-dimensional nanographenes, i.e. graphene molecules, has witnessed rapid developments over the past few years, and these developments can be summarized in four categories: (1) non-conventional methods, (2) structures incorporating seven- or eight-membered rings, (3) selective heteroatom doping, and (4) direct edge functionalization. On the other hand, one-dimensional extension of the graphene molecules leads to the formation of graphene nanoribbons (GNRs) with high aspect ratios. The synthesis of structurally well-defined GNRs has been achieved by extending nanographene synthesis to longitudinally extended polymeric systems. Access to GNRs thus becomes possible through the solution-mediated or surface-assisted cyclodehydrogenation, or "graphitization," of tailor-made polyphenylene precursors. In this review, we describe recent progress in the "bottom-up" chemical syntheses of structurally well-defined nanographenes, namely graphene molecules and GNRs.

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Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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“…Furthermore, Ito et al extended the selection of dipolarophile examples with pure carbon dipolarophiles without electron-withdrawing groups at highert emperature. [8,9] Recently, we demonstrated the transformation of symmetric acene-quinone (2,s ee Figure1)i nto fully conjugated benzoisoindolebased planar N-PAHs by nucleophilic addition to the para-quinone core and following dehydroxylative reduction. [10] However,t he addition of PAMY to ortho-quinones has so far not been explored although it would allow lateral extension of the asymmetricg erminal ketonef unctionalities through further condensation reactions to form N-PAHs with additional quinoxalineunits ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Helical Ullazine‐Quinoxaline‐Based Polycyclic Aromatic Hydrocarbons

Richter

Hahn

Dmitrieva

et al. 2018

Chemistry A European J

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Polycyclica romatic azomethine ylides (PAMYs) are powerful buildingb locks in the bottom-up synthesis of internally nitrogen-containing polycyclica romatic hydrocarbons (N-PAHs) through 1,3-cycloaddition reactions. In this work, the cycloadditionr eactiono fP AMYs to asymmetric ortho-quinones is presented, which, in contrast to the addition to symmetric para-quinones, facilitates subsequent condensation reactions and allows the synthesis of three helical N-PAHs with ullazine-quinoxaline (UQ-1-3)b ackbones. UQ-1 and UQ-2 possess two helical centers;h owever,s ingle-crystal X-ray analysis together with the computational modeling of UQ-3 elucidate the formationo fo nly the thermodynamic-ally most stable geometry with four helical centers in a (P,P,M,M)c onfiguration. For the series UQ-1-3,t he number of redox steps is directly correlated with the number of ullazine or quinoxaline units incorporated into the targeted molecular backbones. Ad etailed investigation of the spectroscopic and magnetic properties of the radical cation and anion as well as the dication and dianion species by in situ EPR/UV/Vis-NIR spectroelectrochemistryi sp rovided. The excellent optical and redoxp roperties combined with helical geometries render them possibly applicable as chiral emitter or ambipolar charge transport material in organic electronics.

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“…Recently our group, [14] as well as Feng and Müllen, [15] independently developed the 1,3-dipolar cycloaddition of the polycyclic aromatic azomethine ylide 1 (Scheme 1) with diarylethynes and subsequent oxidative dehydrogenation to afford fused 1,2,3,4,5-pentaarylpyrroles.W ee nvisioned that subsequent cyclization would lead to the formation of the 6b 2azapentabenzo[bc,ef,hi,kl,no]corannulenes 3.H erein we disclose the first bottom-up synthesis of 8-tert-butyl-6b 2 -azapentabenzo[bc,ef,hi,kl,no]corannulene (3a), which is an ovel bowl-shaped polycyclic aromatic molecule bearing anitrogen atom in an internal position, by the palladium-catalyzed intramolecular cyclization of the fused 1,2,3,4,5-pentaarylpyrrole 2 as the key reaction.…”

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confidence: 99%

Benzene‐Fused Azacorannulene Bearing an Internal Nitrogen Atom

2015

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A novel nitrogen-doped corannulene derivative, 8-tert-butyl-6b(2) -azapentabenzo[bc,ef,hi,kl,no]corannulene, was synthesized by 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a corannulene derivative bearing an internal heteroatom, and exhibits unique structural and physical properties caused by the introduction of the nitrogen atom and extended π-conjugation, as compared to the parent corannulene.

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Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons

Abstract: The synthesis of the novel azomethine ylide, isoquinolino[4,3,2-de]phenanthridine, and its use in 1,3-dipolar cycloaddition with various alkenes and alkynes to form the corresponding fused pyrrolidines and pyrroles is reported.

Cited by 73 publications

References 43 publications

New advances in nanographene chemistry

New advances in nanographene chemistry

Helical Ullazine‐Quinoxaline‐Based Polycyclic Aromatic Hydrocarbons

Benzene‐Fused Azacorannulene Bearing an Internal Nitrogen Atom

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