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2 article(s) from Scott, Lawrence T

Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

Paris E. Georghiou,
Shofiur Rahman,
Abdullah Alodhayb,
Hidetaka Nishimura,
Jaehyun Lee,
Atsushi Wakamiya and
Lawrence T. Scott

Beilstein J. Org. Chem. 2018, 14, 2488–2494, doi:10.3762/bjoc.14.225

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Figure 1: Examples of calix[n]arenes 1 and calix[4]azulenes 2–5.

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Figure 2: Three major computed conformers of OPC4A; a: 1,2-alternate; b: cone and c: saddle.

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Figure 3: Geometry-optimized (ωB97xD/6-31G(d)) and (ωB97xD/GenECP) structures, respectively, computed for lef...

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Published 25 Sep 2018

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Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene

Hee Yeon Cho,
Ronald B. M. Ansems and
Lawrence T. Scott

Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94

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Figure 1: Prototypical open and closed geodesic polyarenes.

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Figure 2: Planar vs pyramidalized π-system.

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Figure 3: Selected examples of geodesic polyarenes synthesized by FVP.

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Scheme 1: Covalent functionalization of fullerene C₆₀ by the Bingel–Hirsch reaction and the Prato reaction.

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Scheme 2: Fullerene-type chemistry at interior carbon atoms of corannulene (1) and diindenochrysene (10).

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Figure 4: POAV angles of fullerene C₆₀ (2), corannulene (1), and diindenochrysene (10).

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Scheme 3: Synthesis of circumtrindene (6) by FVP.

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Scheme 4: Synthetic route to 3,9,15-trichlorodecacyclene (12).

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Figure 5: POAV angle and bond lengths of circumtrindene.

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Scheme 5: Bingel–Hirsch reaction of circumtrindene (6).

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Scheme 6: Proposed mechanism for the Bingel–Hirsch reaction of circumtrindene (6).

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Scheme 7: Prato reaction of circumtrindene (6).

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Figure 6: LUMO orbital map of circumtrindene (B3LYP/6-31G*). The darkest blue areas correspond to the regions...

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Figure 7: Electrostatic potentials on the surfaces of circumtrindene (B3LPY/6-31G*).

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Figure 8: Monoindeno- (25), diindeno- (26), and triindenocircumtrindene (27).

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Figure 9: Two different types of rim carbon atoms on circumtrindene.

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Scheme 8: Site-selective peripheral monobromination of circumtrindene.

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Scheme 9: Suzuki coupling and ring-closing reactions toward indenocircumtrindene (25).

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Scheme 10: Suzuki coupling to prepare compound 30.

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Figure 10: Chemical shifts of ortho-methyl groups in 30 and 31.

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Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C36H12 open geodesic polyarene

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene