Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles

Rafał Stężycki; David Reger; Helen Hoelzel; Norbert Jux; Daniel T. Gryko

doi:10.1055/s-0037-1610286

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(19): 2529-2534
DOI: 10.1055/s-0037-1610286

cluster

Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles

Rafał Stężycki

^aInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44-52, 01-224 Warsaw, Poland eMail: dtgryko@icho.edu.pl

^bWarsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland

,

David Reger

^cDepartment of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany eMail: norbert.jux@fau.de

,

Helen Hoelzel

^cDepartment of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany eMail: norbert.jux@fau.de

,

Norbert Jux*

^cDepartment of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany eMail: norbert.jux@fau.de

,

Daniel T. Gryko *

^aInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44-52, 01-224 Warsaw, Poland eMail: dtgryko@icho.edu.pl

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Abstract

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Published as part of the Cluster Synthesis of Materials

Abstract

Methods for the synthesis of pyrrolo[3,2-b]pyrroles containing hexaphenylbenzene moieties at the 2- and 5-positions or the 1- and 4-positions have been developed. It was shown that placing a hexaphenylbenzene moiety at the 2- and 5-positions requires a Diels–Alder reaction between an alkyne-substituted pyrrolopyrrole core and a 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one. The resulting dyes show a strong blue fluorescence that was hypsochromically shifted by chlorination at the 3- and 6-positions. The overall conjugation between the hexaphenylbenzene moieties and the pyrrolopyrrole core is limited, as evident from their photophysical properties. The hexaphenylbenzene moieties attached to the pyrrolo[3,2-b]pyrrole core could not be transformed into hexa-peri-hexabenzocoronenes through intramolecular oxidative aromatic coupling.

Key words

chromophores - pyrrolopyrroles - halogenation - multicomponent reaction - hexaphenylbenzene - fluorescence

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References and Notes

1a Vij V. Bhalla V. Kumar M. Chem. Rev. 2016; 116: 9565
1b Lungerich D. Hitzenberger JF. Marcia M. Hampel F. Drewello T. Jux N. Angew. Chem. Int. Ed. 2014; 53: 12231
1c Lungerich D. Hitzenberger JF. Donaubauer W. Drewello T. Jux N. Chem. Eur. J. 2016; 22: 16755

2 Tanaka Y. Koike T. Akita M. Chem. Commun. 2010; 46: 4529
3 Traber B. Wolff JJ. Rominger F. Oeser T. Gleiter R. Goebel M. Wortmann R. Chem. Eur. J. 2004; 10: 1227
4 Geng Y. Fechtenkötter A. Müllen K. J. Mater. Chem. 2001; 11: 1634
5 Hiraoka S. Hisanaga Y. Shiro M. Shionoya M. Angew. Chem. Int. Ed. 2010; 49: 1669
6 Tomović Ž. van Dongen J. George SJ. Xu H. Pisula W. Leclère P. Smulders MM. J. De Feyter S. Meijer EW. Schenning AP. H. J. J. Am. Chem. Soc. 2007; 129: 16190
7 Kobayashi K. Sato A. Sakamoto S. Yamaguchi K. J. Am. Chem. Soc. 2003; 125: 3035

8a Chen L. Hernandez Y. Feng X. Müllen K. Angew. Chem. Int. Ed. 2012; 51: 7640
8b Seyler H. Purushothaman B. Jones DJ. Holmes AB. Wong WW. H. Pure Appl. Chem. 2012; 84: 1047
8c Narita A. Feng X. Hernandez Y. Jensen SA. Bonn M. Yang H. Verzhbitskiy IA. Casiraghi C. Hansen MR. Koch AH. R. Fytas G. Ivasenko O. Li B. Mali KS. Balandina T. Mahesh S. De Feyter S. Müllen K. Nat. Chem. 2014; 6: 126
8d Quernheim M. Golling FE. Zhang W. Wagner M. Räder H.-J. Nishiuchi T. Müllen K. Angew. Chem. Int. Ed. 2015; 54: 10341

9a Müller M. Iyer VS. Kübel C. Enkelmann VK. Müllen K. Angew. Chem. Int. Ed. 1997; 36: 1607
9b Müller M. Kübel C. Müllen K. Chem. Eur. J. 1998; 4: 2099

10 Suzuki S. Segawa Y. Itami K. Yamaguchi J. Nat. Chem. 2015; 7: 227
11 Lungerich D. Reger D. Hoelzel H. Riedel R. Martin MM. J. C. Hampel F. Jux N. Angew. Chem. Int. Ed. 2016; 55: 5602

12a Janiga A. Glodkowska-Mrowka E. Stoklosa T. Gryko DT. Asian J. Org. Chem. 2013; 2: 411
12b Krzeszewski M. Thorsted B. Brewer J. Gryko DT. J. Org. Chem. 2014; 79: 3119

13a Tasior M. Gryko DT. J. Org. Chem. 2016; 81: 6580
13b Łukasiewicz Ł. Ryu HG. Mikhaylov A. Azarias C. Banasiewicz M. Kozankiewicz B. Ahn KH. Jacquemin D. Rebane A. Gryko DT. Chem. Asian J. 2017; 12: 1736
13c Poronik YM. Mazur LM. Samoć M. Jacquemin D. Gryko DT. J. Mater. Chem. C 2017; 5: 2620
13d Dereka B. Rosspeintner A. Krzeszewski M. Gryko DT. Vauthey E. Angew. Chem. Int. Ed. 2016; 55: 15624
13e Domínguez R. Montcada NF. de la Cruz P. Palomares E. Langa F. ChemPlusChem 2017; 82: 1096
13f Krzeszewski M. Kodama T. Espinoza EM. Vullev VI. Kubo T. Gryko DT. Chem. Eur. J. 2016; 22: 16478
13g Mishra S. Krzeszewski M. Pignedoli CA. Ruffieux P. Fasel R. Gryko DT. Nat. Commun. 2018; 9: 1714

14a Janiga A. Gryko DT. Chem. Asian J. 2014; 9: 3036
14b Krzeszewski M. Gryko D. Gryko DT. Acc. Chem. Res. 2017; 50: 2334

15 Ivanov AI. Dereka B. Vauthey E. J. Chem. Phys. 2017; 146: 164306
16 Balasubramanyam RK. C. Kumar R. Ippolito SJ. Bhargava SK. Periasamy SR. Narayan R. Basak P. J. Phys. Chem. C 2016; 120: 11313

17a Ji Y. Peng Z. Tong B. Shi J. Zhi J. Dong Y. Dyes Pigm. 2017; 139: 664
17b Li K. Liu Y. Li Y. Feng Q. Hou H. Tang BZ. Chem. Sci. 2017; 8: 7258
17c Sadowski B. Hassanein K. Ventura B. Gryko DT. Org. Lett. 2018; 20: 3183

18 Wu J.-Y. Yu C.-H. Wen J.-J. Chang C.-L. Leung M.-k. Anal. Chem. 2016; 88: 1195

19a Clausen C. Wartchow R. Butenschön H. Eur. J. Org. Chem. 2001; 93
19b Mueller-Westerhoff UT. Zhou M. Tetrahedron Lett. 1993; 34: 571

20 1,4-Bis(3,5-di-tert-butylphenyl)-2,5-bis{4′′-tert-butyl-[2′,3′,5′,6′-tetrakis(4-tert-butylphenyl)]-1,1′:4',1′′-terphenyl-4-yl}-1,4-dihydropyrrolo[3,2-b]pyrrole (10) Pyrrolo[3,2-b]pyrrole 8 (237 mg, 0.250 mmol) and 2,3,4,5-tetrakis(4-tert-butylphenyl)cyclopenta-2,4-dien-1-one (609 mg, 1.00 mmol) were placed in a dry Schlenk flask containing a magnetic stirring bar. The vessel was evacuated and backfilled with argon three times, and Ph₂O (5 mL) was added. The mixture was heated at 250 °C for 42 h then cooled to r.t. EtOH (20 mL) was added, and the precipitated solid was collected by filtration and washed with EtOH. The crude product was refluxed in CH₂Cl₂ for 10 min, collected by filtration, washed with MeOH and pentane, and dried under vacuum to give a white powder, yield: 420 mg (80%); mp ~395 °C (dec.); R_f = 0.37 [silica gel, hexanes–CH₂Cl₂ (4:1)]. ¹H NMR (500 MHz, THF-d ₈): δ = 1.07 (s, 36 H), 1.08 (br s, 54 H), 1.33 (s, 36 H), 6.18 (s, 2 H), 6.60 (AA′BB′, J = 8.3 Hz, 8 H), 6.65 (AA′BB′, J = 8.4 Hz, 8 H), 6.68 (AA′BB′, J = 8.3 Hz, 8 H), 6.70 (AA′BB′, J = 8.5 Hz, 4 H), 6.78 (AA′BB′, J = 8.5 Hz, 8 H), 6.80 (AA′BB′, J = 8.5 Hz, 4 H), 6.85 (AA′BB′, J = 8.3 Hz, 8 H), 7.08 (d, J = 1.3 Hz, 4 H), 7.32 (t, J = 1.3 Hz, 2 H). ¹³C NMR (126 MHz, THF-d ₈): δ = 31.5, 31.6 (2 C), 31.9, 34.7 (3 C), 35.6, 95.4, 119.7 (2 C), 120.4, 123.8 (2 C), 124.1, 125.9, 131.1, 132.0, 132.2, 132.6, 133.1, 135.8, 138.9, 139.1, 139.2, 139.2, 140.0, 140.8, 141.2, 141.4, 141.9, 148.0, 148.2, 148.4, 152.2. HRMS (ESI): m/z [M^•+] calcd for C₁₅₈H₁₈₂N₂: 2107.4303; found: 2107.4348. UV/Vis (THF): λ_max (ε) = 389 nm (69000).
21 Lewtak JP. Gryko D. Bao D. Sebai E. Vakuliuk O. Ścigaj M. Gryko DT. Org. Biomol. Chem. 2011; 9: 8178
22 Grzybowski M. Skonieczny K. Butenschön H. Gryko DT. Angew. Chem. Int. Ed. 2013; 52: 9900
23 Janiga A. Bednarska D. Thorsted B. Brewer J. Gryko DT. Org. Biomol. Chem. 2014; 12: 2874

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