Synthesis of phenanthro[2,3‐<i>h</i>]isoquinoline and phenanthro[3,2‐<i>h</i>]isoquinoline

Tanga, Mary J.; Reist, Elmer J.

doi:10.1002/jhet.5570280105

Journal of Heterocyclic Chem

1991

DOI: 10.1002/jhet.5570280105

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Synthesis of phenanthro[2,3‐h]isoquinoline and phenanthro[3,2‐h]isoquinoline

Mary J. Tanga

Elmer J. Reist

Abstract: The suspected environmental contaminants phenanthro[2,3‐h]isoquinoline 12 and phenanthro[3,2‐h]isoquinoline 11 were synthesized in four steps from a common intermediate 1,4‐phenanthroquinone 3, using a Diels‐Alder reaction.

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Cited by 5 publications

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A Luminescent Nitrogen‐Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity

Wang

Roose

et al. 2015

Chemistry A European J

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We present a nitrogen-containing polycyclic aromatic hydrocarbon (N-PAH), namely 12-methoxy-9-(4-methoxyphenyl)-5,8-diphenyl-4-(pyridin-4-yl)pyreno[1,10,9-h,i,j]isoquinoline (c-TPE-ON), which exhibits high quantum-yield emission both in solution (blue) and in the solid state (yellow). This molecule was unexpectedly obtained by a three-fold, highly regioselective photocyclodehydrogenation of a tetraphenylethylene-derived AIEgen. Based on manifold approaches involving UV/Vis, photoluminescence, and NMR spectroscopy as well as HRMS, we propose a reasonable mechanism for the formation of the disk-like N-PAH that is supported by density functional theory calculations. In contrast to most PAHs that are commonly used, our system does not suffer from entire fluorescence quenching in the solid state due to the peripheral aromatic rings preventing π-π stacking interactions, as evidenced by single-crystal X-ray analysis. Moreover, its rod-like microcrystals exhibit excellent optical waveguide properties. Hence, c-TPE-ON comprises a N-PAH with unprecedented luminescent properties and as such is a promising candidate for fabricating organic optoelectronic devices. Our design and synthetic strategy might lead to a more general approach to the preparation of solution- and solid-state luminescent PAHs.

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A Luminescent Nitrogen‐Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity

Wang

Roose

et al. 2015

Chemistry A European J

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A Metal‐Free Oxidative Dehydrogenative Diels–Alder Reaction for Selective Functionalization of Alkylbenzenes

Manna

Antonchick

2017

Chemistry A European J

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Functionalization of C(sp )-H bonds under metal-free reaction conditions is a great challenge due to poor bond reactivity. A novel metal-free oxidative dehydrogenative Diels-Alder reaction of alkylbenzene derivatives with alkenes through C(sp )-H bond functionalization is described. The developed oxidative method provides a straightforward approach to biologically relevant 1,4-phenanthraquinone and isoindole derivatives from readily available starting materials. Furthermore, the synthesis of nitrostyrenes from enylbenzene derivatives by selective C(sp )-H bond functionalization has been demonstrated.

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ChemInform Abstract: Synthesis of Phenanthro(2,3‐h)isoquinoline and Phenanthro(3,2‐h) isoquinoline.

Tanga

Reist

1991

ChemInform

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Synthesis of phenanthro[2,3‐h]isoquinoline and phenanthro[3,2‐h]isoquinoline

Abstract: The suspected environmental contaminants phenanthro[2,3‐h]isoquinoline 12 and phenanthro[3,2‐h]isoquinoline 11 were synthesized in four steps from a common intermediate 1,4‐phenanthroquinone 3, using a Diels‐Alder reaction.

Cited by 5 publications

References 9 publications

A Luminescent Nitrogen‐Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity

A Luminescent Nitrogen‐Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity

A Metal‐Free Oxidative Dehydrogenative Diels–Alder Reaction for Selective Functionalization of Alkylbenzenes

ChemInform Abstract: Synthesis of Phenanthro(2,3‐h)isoquinoline and Phenanthro(3,2‐h) isoquinoline.

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