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

Sven M. Elbert; Kevin Baumgärtner; Joshua A. Esteves; Laura Weber; Frank Rominger; Michael Mastalerz

doi:10.1055/s-0040-1721851

Organic Materials, Inhaltsverzeichnis

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

Authors

Sven M. Elbert

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Kevin Baumgärtner

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Joshua A. Esteves

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Laura Weber

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Frank Rominger

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Michael Mastalerz

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References and Notes

1a Wu D, Ge H, Liu SH, Yin J. RSC Adv. 2013; 3: 22727
1b Narita A, Wang X.-Y, Feng X, Müllen K. Chem. Soc. Rev. 2015; 44: 6616
1c Majewski MA, Stępień M. Angew. Chem. Int. Ed. 2019; 58: 86
1d Rüdiger EC, Müller M, Freudenberg J, Bunz UH. F. Org. Mater. 2019; 01: 001

2a Simpson CD, Mattersteig G, Martin K, Gherghel L, Bauer RE, Räder HJ, Müllen K. J. Am. Chem. Soc. 2004; 126: 3139
2b Smyth N, Van Engen D, Pascal RA. J. Org. Chem. 1990; 55: 1937

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
4 Dötz F, Brand JD, Ito S, Gherghel L, Müllen K. J. Am. Chem. Soc. 2000; 122: 7707

5a Byun Y, Coskun A. Chem. Mater. 2015; 27: 2576
5b Byun Y, Cho M, Kim D, Jung Y, Coskun A. Macromolecules 2017; 50: 523

6a Wang L, Han Y, Zhang J, Li X, Liu X, Xiao J. Org. Lett. 2020; 22: 261
6b Baumgärtner K, Rominger F, Mastalerz M. Eur. J. Org. Chem. 2019; 4891
6c Baumgärtner K, Meza Chincha AL, Dreuw A, Rominger F, Mastalerz M. Angew. Chem. Int. Ed. 2016; 55: 15594

7 Wasserfallen D, Kastler M, Pisula W, Hofer WA, Fogel Y, Wang Z, Müllen K. J. Am. Chem. Soc. 2006; 128: 1334
8 Baumgärtner K, Kirschbaum T, Krutzek F, Dreuw A, Rominger F, Mastalerz M. Chem. Eur. J. 2017; 23: 17817
9 Moursounidis J, Wege D. Aust. J. Chem. 1988; 41: 235

10a Itami K, Segawa Y, Watanabe K, Cheung KY, Watanabe K, Segawa Y, Itami K. ChemRxiv 2020; , preprint; https://doi.org/10.26434/chemrxiv.12324353.v2
10b Franz D, Robbins SJ, Boeré RT, Dibble PW. J. Org. Chem. 2009; 74: 7544

11 Wang J, Miao Q. Org. Lett. 2019; 21: 10120
12 Han W, Tran J, Zhang H, Jeffrey S, Swartling D, Ford GP, Biehl E. Synthesis 1995; 827
13 Han Y, Dong S, Shao J, Fan W, Chi C. Angew. Chem. Int. Ed. 2020;

14a Wickham PP, Hazen KH, Guo H, Jones G, Reuter KH, Scott WJ. J. Org. Chem. 1991; 56: 2045
14b Truong T, Mesgar M, Le KK. A, Daugulis O. J. Am. Soc. Chem. 2014; 136: 8568
14c Reuter KH, Scott WJ. J. Org. Chem. 1993; 58: 4722
14d Pun SH, Wang Y, Chu M, Chan CK, Li Y, Liu Z, Miao Q. J. Am. Chem. Soc. 2019; 141: 9680
14e Mesgar M, Nguyen-Le J, Daugulis O. Chem. Commun. 2019; 55: 9467

15 Pérez D, Peña D, Guitián E. Eur. J. Org. Chem. 2013; 5981

16a Pascal Jr RA. Chem. Rev. 2006; 106: 4809
16b Xiao J, Liu S, Liu Y, Ji L, Liu X, Zhang H, Sun X, Zhang Q. Chem. Asian J. 2012; 7: 561
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
16d Xiao J, Divayana Y, Zhang Q, Doung HM, Zhang H, Boey F, Sun XW, Wudl F. J. Mater. Chem. 2010; 20: 8167
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
16f Qiao X, Padula MA, Ho DM, Vogelaar NJ, Schutt CE, Pascal RA. J. Am. Chem. Soc. 1996; 118: 741
16g Qiao X, Ho DM, Pascal Jr RA. Angew. Chem. Int. Ed. Engl. 1997; 36: 1531
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
16i Duong HM, Bendikov M, Steiger D, Zhang Q, Sonmez G, Yamada J, Wudl F. Org. Lett. 2003; 5: 4433
16j Clevenger RG, Kumar B, Menuey EM, Kilway KV. Chem. Eur. J. 2018; 24: 3113

17 Xiao Y, Mague JT, Schmehl RH, Haque FM, Pascal Jr RA. Angew. Chem. Int. Ed. 2019; 58: 2831
18 Ji L, Krummenacher I, Friedrich A, Lorbach A, Haehnel M, Edkins K, Braunschweig H, Marder TB. J. Org. Chem. 2018; 83: 3599
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)
20 Korb M, Lang H. Chem. Soc. Rev. 2019; 48: 2829

21a van der Sluis P, Spek AL. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990; 46: 194
21b Spek A. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009; 65: 148

Zusatzmaterial

Ergänzendes Material (PDF)