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Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl‐Shaped Core

The synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl‐shaped molecular scaffold has been achieved by use of different strategies. Although the ‐ and ‐symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by ch... Full description

Journal Title: European Journal of Organic Chemistry November 2014, Vol.2014(33), pp.7469-7480
Main Author: Mughal, Ehsan Ullah
Other Authors: Neumann, Beate , Stammler, Hans‐Georg , Kuck, Dietmar
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1434-193X ; E-ISSN: 1099-0690 ; DOI: 10.1002/ejoc.201402995
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recordid: wj10.1002/ejoc.201402995
title: Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl‐Shaped Core
format: Article
creator:
  • Mughal, Ehsan Ullah
  • Neumann, Beate
  • Stammler, Hans‐Georg
  • Kuck, Dietmar
subjects:
  • Synthetic Methods
  • C–C Cou­pling
  • Polycycles
  • Hydrocarbons
  • Steric Hindrance
  • Crowded Molecules
  • Bowl‐Shaped Molecules
ispartof: European Journal of Organic Chemistry, November 2014, Vol.2014(33), pp.7469-7480
description: The synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl‐shaped molecular scaffold has been achieved by use of different strategies. Although the ‐ and ‐symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding ‐ and ‐symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained in pure form. Threefold cyclocondensation of these TBTQ‐based tris‐tolanes with tetracyclone gave ‐ and ‐tris(pentaphenylphenyl)tribenzotriquinacenes in good yields. Attempts to generate a completely closed graphene‐like periphery around the TBTQ core by Scholl cyclodehydrogenation of the ‐symmetrical isomer failed. ‐ and ‐symmetrical tribenzotriquinacene‐based tris‐tolanes were synthesized and found to be separable, in contrast to TBTQ trialdehydes, triacetylenes and triiodo precursors. Both 2,6,10‐ and 2,6,11‐tris‐tolanes were converted into the tris‐pentaphenylphenyl‐TBTQ hydrocarbons, as shown for the ‐isomer. Attempts to generate warped TBTQ‐centered graphene cuttings from the derivative failed.
language: eng
source:
identifier: ISSN: 1434-193X ; E-ISSN: 1099-0690 ; DOI: 10.1002/ejoc.201402995
fulltext: fulltext
issn:
  • 1434-193X
  • 1434193X
  • 1099-0690
  • 10990690
url: Link


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titleTribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl‐Shaped Core
creatorMughal, Ehsan Ullah ; Neumann, Beate ; Stammler, Hans‐Georg ; Kuck, Dietmar
ispartofEuropean Journal of Organic Chemistry, November 2014, Vol.2014(33), pp.7469-7480
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subjectSynthetic Methods ; C–C Cou­pling ; Polycycles ; Hydrocarbons ; Steric Hindrance ; Crowded Molecules ; Bowl‐Shaped Molecules
descriptionThe synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl‐shaped molecular scaffold has been achieved by use of different strategies. Although the ‐ and ‐symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding ‐ and ‐symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained in pure form. Threefold cyclocondensation of these TBTQ‐based tris‐tolanes with tetracyclone gave ‐ and ‐tris(pentaphenylphenyl)tribenzotriquinacenes in good yields. Attempts to generate a completely closed graphene‐like periphery around the TBTQ core by Scholl cyclodehydrogenation of the ‐symmetrical isomer failed. ‐ and ‐symmetrical tribenzotriquinacene‐based tris‐tolanes were synthesized and found to be separable, in contrast to TBTQ trialdehydes, triacetylenes and triiodo precursors. Both 2,6,10‐ and 2,6,11‐tris‐tolanes were converted into the tris‐pentaphenylphenyl‐TBTQ hydrocarbons, as shown for the ‐isomer. Attempts to generate warped TBTQ‐centered graphene cuttings from the derivative failed.
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descriptionThe synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl‐shaped molecular scaffold has been achieved by use of different strategies. Although the ‐ and ‐symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding ‐ and ‐symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained in pure form. Threefold cyclocondensation of these TBTQ‐based tris‐tolanes with tetracyclone gave ‐ and ‐tris(pentaphenylphenyl)tribenzotriquinacenes in good yields. Attempts to generate a completely closed graphene‐like periphery around the TBTQ core by Scholl cyclodehydrogenation of the ‐symmetrical isomer failed. ‐ and ‐symmetrical tribenzotriquinacene‐based tris‐tolanes were synthesized and found to be separable, in contrast to TBTQ trialdehydes, triacetylenes and triiodo precursors. Both 2,6,10‐ and 2,6,11‐tris‐tolanes were converted into the tris‐pentaphenylphenyl‐TBTQ hydrocarbons, as shown for the ‐isomer. Attempts to generate warped TBTQ‐centered graphene cuttings from the derivative failed.
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abstractThe synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl‐shaped molecular scaffold has been achieved by use of different strategies. Although the ‐ and ‐symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding ‐ and ‐symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained in pure form. Threefold cyclocondensation of these TBTQ‐based tris‐tolanes with tetracyclone gave ‐ and ‐tris(pentaphenylphenyl)tribenzotriquinacenes in good yields. Attempts to generate a completely closed graphene‐like periphery around the TBTQ core by Scholl cyclodehydrogenation of the ‐symmetrical isomer failed. ‐ and ‐symmetrical tribenzotriquinacene‐based tris‐tolanes were synthesized and found to be separable, in contrast to TBTQ trialdehydes, triacetylenes and triiodo precursors. Both 2,6,10‐ and 2,6,11‐tris‐tolanes were converted into the tris‐pentaphenylphenyl‐TBTQ hydrocarbons, as shown for the ‐isomer. Attempts to generate warped TBTQ‐centered graphene cuttings from the derivative failed.
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pubWILEY‐VCH Verlag
doi10.1002/ejoc.201402995
pages7469-7480
date2014-11