HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

Alexandre Rossignon; Beatrice Berionni Berna; A. Jorge Parola; César A. T. Laia; Davide Bonifazi

doi:10.1055/a-1976-0291

Organic Materials, Inhaltsverzeichnis

CC BY-NC-ND 4.0 · Organic Materials 2022; 4(04): 240-254
DOI: 10.1055/a-1976-0291

Original Article

HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

Authors

Alexandre Rossignon

^aDepartment of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium

^bSchool of Chemistry of Cardiff University, Cardiff University, CF10 3 AT Cardiff, United Kingdom
Beatrice Berionni Berna

^cInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria
A. Jorge Parola

^dLAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal
César A. T. Laia

^dLAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal
Davide Bonifazi

^cInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria

Abstract

Alle Artikel dieser Rubrik

Abstract

A series of novel O-doped polycyclic aromatic hydrocarbons, bearing a different number of electron-donating alkoxy substituents, has been prepared using a novel copper-promoted anaerobic protocol for the cyclisation of highly electron rich peri-xanthenoxanthene molecular modules. The effect of the number and position of the alkoxy substituents on the optoelectronic properties has thus been investigated, unveiling p-type semiconducting properties. All molecules displayed a significant colour change upon oxidation, suggesting that these compounds can be used to devise chromogenic materials to engineer electrochromic devices.

Key words

polycyclic aromatic hydrocarbons - PXX - electrochromism - oxygen heterocycles - electrochromic devices

Volltext

Referenzen

References

1a Narita A, Wang X-Y, Feng X, Müllen K. Chem. Soc. Rev. 2015; 44: 6616
1b Stępień M, Gońka E, Żyła M, Sprutta N. Chem. Rev. 2017; 117: 3479
1c Tsuji H, Nakamura E. Acc. Chem. Res. 2017; 50: 396
1d Kulyk O, Rocard L, Maggini L, Bonifazi D. Chem. Soc. Rev. 2020; 49: 8400
1e Fermi A, Bonifazi D. Tailoring the photoredox properties of organic dyes.. Photochemistry. Volume 47. The Royal Society of Chemistry; London: 2020: 293
1f Borissov A, Maurya YK, Moshniaha L, Wong W-S, Żyła-Karwowska M, Stępień M. Chem. Rev. 2022; 122: 565

2a Pummerer R, Frankfurter F. Berichte der Dtsch. Chem. Gesellschaft 1914; 47: 1472
2b Pummerer R, Rieche A. Berichte der Dtsch. Chem. Gesellschaft 1926; 59: 2161

3 Takaishi K, Hinoide S, Matsumoto T, Ema T. J. Am. Chem. Soc. 2019; 141: 11852

4a Sciutto A, Fermi A, Folli A, Battisti T, Beames JM, Murphy DM, Bonifazi D. Chem. Eur. J. 2018; 24: 4382
4b Trifonov AL, Panferova LI, Levin VV, Kokorekin VA, Dilman AD. Org. Lett. 2020; 22: 2409
4c Schlesinger I, Powers-Riggs NE, Logsdon JL, Qi Y, Miller SA, Tempelaar R, Young RM, Wasielewski MR. Chem. Sci. 2020; 11: 9532
4d Pezzetta C, Folli A, Matuszewska O, Murphy D, Davidson RWM, Bonifazi D. Adv. Synth. Catal. 2021; 363: 4740
4e Ma Q, Song J, Zhang X, Jiang Y, Ji L, Liao S. Nat. Commun. 2021; 12: 429

5a Song C, Swager TM. Macromolecules 2009; 42: 1472
5b Noda M, Kobayashi N, Katsuhara M, Yumoto A, Ushikura S, Yasuda R, Hirai N, Yukawa G, Yagi I, Nomoto K, Urabe T. SID Symp. Dig. Tech. Pap. 2010; 41: 710
5c Wang L, Duan G, Ji Y, Zhang H. J. Phys. Chem. C 2012; 116: 22679
5d Lv N, Xie M, Gu W, Ruan H, Qiu S, Zhou C, Cui Z. Org. Lett. 2013; 15: 2382
5e Christensen JA, Zhang J, Zhou J, Nelson JN, Wasielewski MR. J. Phys. Chem. C 2018; 122: 23364

6a Dettling A, Rieker A, Speiser B. Tetrahedron Lett. 1988; 29: 4533
6b Frenking G, Rieker A, Salbeck J, Speiser B. Z. Naturforsch., B: Chem Sci. 1996; 51: 377

7 Keller SN, Veltri NL, Sutherland TC. Org. Lett. 2013; 15: 4798

8a Stassen D, Demitri N, Bonifazi D. Angew. Chem. Int. Ed. 2016; 55: 5947
8b Kamei T, Uryu M, Shimada T. Org. Lett. 2017; 19: 2714

9 Rossignon A, Bonifazi D. Synthesis 2019; 51: 3588
10 Miletić T, Fermi A, Orfanos I, Avramopoulos A, De Leo F, Demitri N, Bergamini G, Ceroni P, Papadopoulos MG, Couris S, Bonifazi D. Chem. Eur. J. 2017; 23: 2363
11 Berezin A, Biot N, Battisti T, Bonifazi D. Angew. Chem. Int. Ed. 2018; 57: 8942
12 Sciutto A, Berezin A, Lo Cicero M, Miletić T, Stopin A, Bonifazi D. J. Org. Chem. 2018; 83: 13787
13 Valentini C, Gowland D, Bezzu CG, Romito D, Demitri N, Bonini N, Bonifazi D. Chem. Sci. 2022; 13: 6335

14a Dobelmann L, Parham AH, Büsing A, Buchholz H, König B. RSC Adv. 2014; 4: 60473
14b Đorđević L, Milano D, Demitri N, Bonifazi D. Org. Lett. 2020; 22: 4283
14c Fletcher-Charles J, Ferreira RR, Abraham M, Romito D, Oppel M, González L, Bonifazi D. Eur. J. Org. Chem. 2022; 2022: e202101166

15 Hume P, Furkert DP, Brimble MA. Tetrahedron Lett. 2012; 53: 3771
16 Kobayashi N, Sasaki M, Nomoto K. Chem. Mater. 2009; 21: 552
17 Hassab S, Shen DE, Österholm AM, Da Rocha M, Song G, Alesanco Y, Viñuales A, Rougier A, Reynolds JR, Padilla J. Sol. Energy Mater. Sol. Cells 2018; 185: 54
18 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 16, Revision B.01.. Gaussian, Inc.. Wallingford, CT: 2016

Zusatzmaterial

Supporting Information for this article is available online. (PDF)