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1 article(s) from Miller, Glen P

Kinetically stabilized 1,3-diarylisobenzofurans and the possibility of preparing large, persistent isoacenofurans with unusually small HOMO–LUMO gaps

Qian Liu and
Glen P. Miller

Beilstein J. Org. Chem. 2024, 20, 1099–1110, doi:10.3762/bjoc.20.97

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Figure 1: Neutral, closed-shell resonance forms for pentacene highlighting Clar aromatic sextets (see [1]) and t...

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Figure 2: The only neutral, closed-shell resonance form for 5-ring isotetracenofuran with its highly delocali...

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Figure 3: DFT calculated HOMO–LUMO gaps of acenes and isoacenofurans performed at the B3LYP/6-311+G(d,p)//B3L...

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Figure 4: A structural rendering of 1,3-dimesitylisobenzofuran showing the requirement for non-planar mesityl...

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Scheme 1: Synthesis of 1,3-diarylisobenzofurans 3 and 23.

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Figure 5: UV–vis (top) and fluorescence (middle) spectra for 10⁻⁶ M solutions of 1,3-diarylisobenzofurans 2, 3...

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Figure 6: Calculated HOMO and LUMO orbitals for parent isobenzofuran (1) and 1,3-diarylisobenzofuran derivati...

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Figure 7: UV–vis spectra calculated for 1,3-diarylisobenzofuran derivatives 1, 2, 3, 23, 24 and 25 using a DF...

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Figure 8: UV–vis spectra for the reactions of 2 (top) and 3 (bottom) with a 7000-fold excess of DMAD in CH₂Cl₂...

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Scheme 2: Reactions between 1,3-diarylisobenzofurans 2, 3 and 23 and DMAD to produce Diels–Alder adducts 26, ...

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Scheme 3: Synthesis of 1,3-dimesitylisobenzofuran (3).

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Scheme 4: Synthesis of 1,2-phenylenebis(mesitylmethanone) (21).

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Scheme 5: Synthesis of 1,2-phenylenebis((2,4,6-triethylphenyl)methanone) (22).

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Scheme 6: Synthesis of 1,3-bis(2,4,6-triethylphenyl)isobenzofuran (23).

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Scheme 7: Synthesis of dimethyl 1,4-diphenyl-1,4-dihydro-1,4-epoxynaphthalene-2,3-dicarboxylate (26).

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Scheme 8: Synthesis of dimethyl 1,4-dimesityl-1,4-dihydro-1,4-epoxynaphthalene-2,3-dicarboxylate (27).

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Published 17 May 2024

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