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3 article(s) from Yamada, Michio

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Masahiro Kako,
Masato Kai,
Masanori Yasui,
Michio Yamada,
Yutaka Maeda and
Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

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Figure 1: Positional notation of 6,6-bonds in a mono-adduct of C₆₀ with the first addition site indicated usi...

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Scheme 1: Synthesis of silylene adducts 2 and 3.

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Figure 2: Absorption spectrum of 3 in CH₂Cl₂.

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Figure 3: 500 MHz ¹H NMR spectrum of 3 in CDCl₃/CS₂ 3:1.

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Figure 4: 125 MHz ¹³C NMR spectrum of 3 in CDCl₃/CS₂ 3:1. The signals of sp² carbons of C₆₀ and quaternary ca...

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Figure 5: ORTEP drawing of 3 showing thermal ellipsoids at the 50% probability level at 100 K. Hydrogen atoms...

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Figure 6: (a) Partial structures of isomers of Dip₂SiC₆₀. (b) Optimized structures of 2a and 2c. Hydrogen ato...

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Figure 7: Optimized structures of 3_cis_-2, 3_cis_-3, 3_e, 3_trans_-1, 3_trans_-2, 3_trans_-3, and 3_trans_-4. Values in p...

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Figure 8: (a) LUMO and (b) HOMO of 2a calculated at the B3LYP/6-31G(d) level. Hydrogen atoms are omitted for ...

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Figure 9: Cyclic voltammograms (CV) and differential pulse voltammograms (DPV) of 3 in o-dichlorobenzene cont...

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Full Research Paper

Published 22 May 2024

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Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

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Scheme 1: Pathway of the [2 + 2] CA–RE reaction of an electron-rich alkyne with TCNE or TCNQ. EDG = electron-...

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Scheme 2: Reaction pathway for DMA-appended acetylene and TCNEO.

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Scheme 3: Pathway of the [2 + 2] CA–RE reaction between 1 and DCFs.

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Scheme 4: Sequential double [2 + 2] CA–RE reactions between 1 and TCNE.

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Scheme 5: Divergent chemical transformation pathways of TCBD 6.

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Scheme 6: Synthesis of 12.

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Scheme 7: [2 + 2] CA–RE reaction of 1 with 14. TCE = 1,1,2,2-tetrachloroethane.

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Scheme 8: Autocatalytic model proposed by Nielsen et al.

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Scheme 9: Synthesis of anthracene-embedded TCBD compound 19.

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Scheme 10: Sequence of the [2 + 2] CA–RE reaction between dibenzo-fused cyclooctyne or cyclooctadiyne and TCNE...

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Scheme 11: [2 + 2] CA–RE reaction between the CPP derivatives and TCNE. THF = tetrahydrofuran.

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Scheme 12: [2 + 2] CA–RE reaction between ethynylfullerenes 31 and TCNE and subsequent thermal rearrangement.

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Scheme 13: Pathway of the [2 + 2] CA–RE reaction between TCNE and 34, followed by additional skeletal transfor...

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Scheme 14: Synthesis scheme for heterocycle 38 from the reaction between TCNE and 1 in water and a surfactant.

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Scheme 15: Synthesis scheme of the CDA product 41.

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Scheme 16: Synthesis of rotaxanes 44 and 46 via the [2 + 2] CA–RE reaction.

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Scheme 17: Synthesis of a Cu^I bisphenanthroline-based rotaxane 50.

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Figure 1: Structures of the chiral push–pull chromophores 51–56.

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Figure 2: Structures of the axially chiral TCBD 57 and DCNQ 58 bearing a C₆₀ core.

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Figure 3: Structures of the axially chiral SubPc–TCBD–aniline conjugates 59 and 60 and the subporphyrin–TCBD–...

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Figure 4: Structures of 63 and the TCBD 64.

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Figure 5: Structures of the fluorophore-containing TCBDs 65–67.

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Figure 6: Structures of the fluorophore-containing TCBDs 68–72.

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Figure 7: Structures of the urea-containing TCBDs 73–75.

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Figure 8: Structures of the fullerene–TCBD and DCNQ conjugates 76–79 and their reference compounds 80–83.

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Figure 9: Structures of the ZnPc–TCBD–aniline conjugates 84 and 85.

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Figure 10: Structures of the ZnP–PCBD and TCBD conjugates 86–88.

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Figure 11: Structures of the porphyrin-based donor–acceptor conjugates (89–104).

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Figure 12: Structures of the porphyrin–PTZ or DMA conjugates 105–112.

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Figure 13: Structures of the BODIPY–Acceptor–TPA or PTZ conjugates 113–116.

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Figure 14: Structures of the corrole–TCBD conjugates 117 and 118.

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Figure 15: Structure of the dendritic TCBD 119.

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Figure 16: Structures of the TCBDs 120–126.

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Figure 17: Structures of the precursor 127 and TCBDs 128–130.

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Figure 18: Structures of 131–134 utilized for BHJ OSCs.

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Review

Published 22 Jan 2024

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Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

Yutaka Maeda,
Saeka Akita,
Mitsuaki Suzuki,
Michio Yamada,
Takeshi Akasaka,
Kaoru Kobayashi and
Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

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Scheme 1: Reaction of the La@C₂_v-C₈₂ anion with benzyl bromide derivatives.

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Figure 1: Changes in absorption spectra during the reaction of La@C₂_v-C₈₂ anion with 1a.

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Figure 2: HPLC profiles of the reaction mixture. Conditions: Buckyprep column (⌀ = 4.6 × 250 mm); eluent, tol...

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Figure 3: HPLC profiles (Buckyprep column (⌀ = 4.6 × 250 mm); eluent, toluene; flow rate, 1.0 mL/min; UV dete...

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Figure 4: Absorption spectra of 2, 3, 4, and 5 in CS₂ and absorption spectra of C14, C10, C18, and C9 in Ce@C₂...

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Figure 5: ORTEP drawing of 3a with thermal ellipsoids shown at 50% probability level. Only an independent uni...

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Figure 6: (a) Charge density of La@C₂_v-C₈₂ anion as a function of its POAV values and (b) an enlarged part vi...

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Full Research Paper

Published 11 Dec 2023

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Two-fold addition reaction of silylene to C60: structural and electronic properties of a bis-adduct

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

Controlling the reactivity of La@C82 by reduction: reaction of the La@C82 anion with alkyl halide with high regioselectivity

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity