2010
DOI: 10.1002/chem.201001057
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Domino Diels–Alder Cycloadditions of Arynes: New Approach to Elusive Perylene Derivatives

Abstract: A game of dominos: Domino [4+2]/[4+2] cycloadditions between 1,8‐difurylnaphthalene and arynes provide the corresponding adducts in a highly diastereoselective manner. This new synthetic methodology enables the preparation of elusive perylene derivatives with a remarkable reduced HOMO–LUMO gap, a crucial feature for organic semiconductors.

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Cited by 61 publications
(35 citation statements)
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“…On the other hand, the peri ‐condensed dibenzo[ fg , uv ]pentaphene (naphtho[ a ]perylene, 177 ) was constructed by our group by the reaction of the previously mentioned bis‐furan 140 with 2,3‐naphthyne ( 37 ; Scheme ). This reaction is similar to that previously described in section 4.2 (see Scheme ) 71. Remarkably, compound 177 has a HOMO–LUMO gap of 2.02 eV, that is, lower than that of the paradigmatic organic semi‐conductor pentacene.…”
Section: Aryne‐mediated Synthesis Of Seven‐ring Polycyclic Aromatisupporting
confidence: 85%
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“…On the other hand, the peri ‐condensed dibenzo[ fg , uv ]pentaphene (naphtho[ a ]perylene, 177 ) was constructed by our group by the reaction of the previously mentioned bis‐furan 140 with 2,3‐naphthyne ( 37 ; Scheme ). This reaction is similar to that previously described in section 4.2 (see Scheme ) 71. Remarkably, compound 177 has a HOMO–LUMO gap of 2.02 eV, that is, lower than that of the paradigmatic organic semi‐conductor pentacene.…”
Section: Aryne‐mediated Synthesis Of Seven‐ring Polycyclic Aromatisupporting
confidence: 85%
“…More interestingly from a synthetic point of view, in 2010 our group reported the preparation of benzo[ a ]perylene ( 143 ), a peri ‐condensed PAH with six fused benzene rings, by a highly convergent approach based on the tandem double cycloaddition of an aryne with 1,8‐difurylnaphthalene ( 140 ; Scheme ) 71. Thus, when (trimethylsilyl)phenyl triflate 63a was treated with CsF in the presence of 140 , compound 142 was isolated in quantitative yield as the only diastereoisomer.…”
Section: Aryne‐mediated Synthesis Of Six‐ring Polycyclic Aromatic mentioning
confidence: 99%
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