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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(04): 358-361
DOI: 10.1055/s-0040-1721851
Focus Issue: Curved Organic π-Systems
Short Communication

Pyrene-Based Diarynes as Precursors for Twisted Fused Polycyclic Aromatic Hydrocarbons: A Comparison of Two Routes

Sven M. Elbert
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Kevin Baumgärtner
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Joshua A. Esteves
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Laura Weber
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Frank Rominger
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Michael Mastalerz
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
› Institutsangaben Funding Information The authors are grateful to the “Deutsche Forschungsgemeinschaft” for supporting this project within the collaborative research center: SFB1249 “N-heteropolycyclic compounds as functional materials” (TP-A04).
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Abstract

Two bench-stable and readily accessible pyrene-based diaryne precursors based on triflate as well as TMS triflate motifs are introduced and compared in their [4+2]-Diels–Alder reactions with tetracyclone to give an oligophenyl-substituted dibenzo[e,l]pyrene in both cases. By single-crystal X-ray analysis, this twistacene showed helical chirality and an end-to-end contortion of 49.6° due to steric repulsion.

Key words

polycyclic aromatic hydrocarbons - twistacene - Diels–Alder reaction - pyrenes - arynes

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1721851.


Supporting Information



Publikationsverlauf

Eingereicht: 20. Oktober 2020

Angenommen: 12. November 2020

Artikel online veröffentlicht:
23. Dezember 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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  • References and Notes

    • 1a Wu D, Ge H, Liu SH, Yin J. RSC Adv. 2013; 3: 22727
      CrossrefPubMed
    • 1b Narita A, Wang X.-Y, Feng X, Müllen K. Chem. Soc. Rev. 2015; 44: 6616
      CrossrefPubMed
    • 1c Majewski MA, Stępień M. Angew. Chem. Int. Ed. 2019; 58: 86
      CrossrefPubMed
    • 1d Rüdiger EC, Müller M, Freudenberg J, Bunz UH. F. Org. Mater. 2019; 01: 001
      CrossrefPubMed
    • 2a Simpson CD, Mattersteig G, Martin K, Gherghel L, Bauer RE, Räder HJ, Müllen K. J. Am. Chem. Soc. 2004; 126: 3139
      CrossrefPubMed
    • 2b Smyth N, Van Engen D, Pascal RA. J. Org. Chem. 1990; 55: 1937
      CrossrefPubMed
  • 3 Chen W, Li X, Long G, Li Y, Ganguly R, Zhang M, Aratani N, Yamada H, Liu M, Zhang Q. Angew. Chem. Int. Ed. 2018; 57: 13555
    Artikel in Thieme ConnectPubMed
  • 4 Dötz F, Brand JD, Ito S, Gherghel L, Müllen K. J. Am. Chem. Soc. 2000; 122: 7707
    CrossrefPubMed
    • 5a Byun Y, Coskun A. Chem. Mater. 2015; 27: 2576
      CrossrefPubMed
    • 5b Byun Y, Cho M, Kim D, Jung Y, Coskun A. Macromolecules 2017; 50: 523
      CrossrefPubMed
    • 6a Wang L, Han Y, Zhang J, Li X, Liu X, Xiao J. Org. Lett. 2020; 22: 261
      CrossrefPubMed
    • 6b Baumgärtner K, Rominger F, Mastalerz M. Eur. J. Org. Chem. 2019; 4891
      PubMed
    • 6c Baumgärtner K, Meza Chincha AL, Dreuw A, Rominger F, Mastalerz M. Angew. Chem. Int. Ed. 2016; 55: 15594
      CrossrefPubMed
  • 7 Wasserfallen D, Kastler M, Pisula W, Hofer WA, Fogel Y, Wang Z, Müllen K. J. Am. Chem. Soc. 2006; 128: 1334
    Artikel in Thieme ConnectPubMed
  • 8 Baumgärtner K, Kirschbaum T, Krutzek F, Dreuw A, Rominger F, Mastalerz M. Chem. Eur. J. 2017; 23: 17817
    CrossrefPubMed
  • 9 Moursounidis J, Wege D. Aust. J. Chem. 1988; 41: 235
    CrossrefPubMed
  • 11 Wang J, Miao Q. Org. Lett. 2019; 21: 10120
    CrossrefPubMed
  • 12 Han W, Tran J, Zhang H, Jeffrey S, Swartling D, Ford GP, Biehl E. Synthesis 1995; 827
    PubMed
  • 13 Han Y, Dong S, Shao J, Fan W, Chi C. Angew. Chem. Int. Ed. 2020; DOI: 10.1002/anie.202012651.
    CrossrefPubMed
    • 14a Wickham PP, Hazen KH, Guo H, Jones G, Reuter KH, Scott WJ. J. Org. Chem. 1991; 56: 2045
      CrossrefPubMed
    • 14b Truong T, Mesgar M, Le KK. A, Daugulis O. J. Am. Soc. Chem. 2014; 136: 8568
      CrossrefPubMed
    • 14c Reuter KH, Scott WJ. J. Org. Chem. 1993; 58: 4722
      CrossrefPubMed
    • 14d Pun SH, Wang Y, Chu M, Chan CK, Li Y, Liu Z, Miao Q. J. Am. Chem. Soc. 2019; 141: 9680
      CrossrefPubMed
    • 14e Mesgar M, Nguyen-Le J, Daugulis O. Chem. Commun. 2019; 55: 9467
      CrossrefPubMed
  • 15 Pérez D, Peña D, Guitián E. Eur. J. Org. Chem. 2013; 5981
    PubMed
    • 16a Pascal Jr RA. Chem. Rev. 2006; 106: 4809
      CrossrefPubMed
    • 16b Xiao J, Liu S, Liu Y, Ji L, Liu X, Zhang H, Sun X, Zhang Q. Chem. Asian J. 2012; 7: 561
      CrossrefPubMed
    • 16c Xiao J, Duong HM, Liu Y, Shi W, Ji L, Li G, Li S, Liu X.-W, Ma J, Wudl F, Zhang Q. Angew. Chem. Int. Ed. 2012; 51: 6094
      CrossrefPubMed
    • 16d Xiao J, Divayana Y, Zhang Q, Doung HM, Zhang H, Boey F, Sun XW, Wudl F. J. Mater. Chem. 2010; 20: 8167
      CrossrefPubMed
    • 16e Walters RS, Kraml CM, Byrne N, Ho DM, Qin Q, Coughlin FJ, Bernhard S, Pascal Jr RA. J. Am. Chem. Soc. 2008; 130: 16435
      CrossrefPubMed
    • 16f Qiao X, Padula MA, Ho DM, Vogelaar NJ, Schutt CE, Pascal RA. J. Am. Chem. Soc. 1996; 118: 741
      CrossrefPubMed
    • 16g Qiao X, Ho DM, Pascal Jr RA. Angew. Chem. Int. Ed. Engl. 1997; 36: 1531
      CrossrefPubMed
    • 16h Lu J, Ho DM, Vogelaar NJ, Kraml CM, Bernhard S, Byrne N, Kim LR, Pascal Jr RA. J. Am. Chem. Soc. 2006; 128: 17043
      CrossrefPubMed
    • 16i Duong HM, Bendikov M, Steiger D, Zhang Q, Sonmez G, Yamada J, Wudl F. Org. Lett. 2003; 5: 4433
      CrossrefPubMed
    • 16j Clevenger RG, Kumar B, Menuey EM, Kilway KV. Chem. Eur. J. 2018; 24: 3113
      CrossrefPubMed
  • 17 Xiao Y, Mague JT, Schmehl RH, Haque FM, Pascal Jr RA. Angew. Chem. Int. Ed. 2019; 58: 2831
    CrossrefPubMed
  • 18 Ji L, Krummenacher I, Friedrich A, Lorbach A, Haehnel M, Edkins K, Braunschweig H, Marder TB. J. Org. Chem. 2018; 83: 3599
    CrossrefPubMed
  • 19 Compound 4 can be isolated in 96% yield in sufficient purity to be used in further synthetic steps. To obtain an analytical pure sample, purification by column chromatography has to be taken into account, accompanied by a material loss and an isolated yield of 31% (see the SI)
    PubMed
  • 20 Korb M, Lang H. Chem. Soc. Rev. 2019; 48: 2829
    CrossrefPubMed
    • 21a van der Sluis P, Spek AL. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990; 46: 194
      CrossrefPubMed
    • 21b Spek A. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009; 65: 148
      CrossrefPubMed