Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(21): 4042-4047
DOI: 10.1055/a-1543-4018
DOI: 10.1055/a-1543-4018
feature
Anthracene-Based Zwitterion with a Small HOMO–LUMO Energy Gap
This work was financially supported in part by the JSPS KAKENHI Grant Number JP20H02723.
Abstract
We have designed and synthesized an anthracene-based zwitterion, 2-methyl-2-azoniaanthracene-7-olate. The zwitterion shows amphoteric redox properties and low-energy-light absorption originating from the small HOMO–LUMO energy gap of ca. 1.7 eV. DFT calculations show that the combination of replacing the C–H with N+–Me and introducing O− is necessary to alter the electronic structure and properties of anthracene significantly.
Key words
zwitterion - small HOMO–LUMO energy gap - redox - long-wavelength light absorption - negative solvatochromismSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1543-4018.
- Supporting Information
Publication History
Received: 22 May 2021
Accepted: 02 July 2021
Accepted Manuscript online:
02 July 2021
Article published online:
12 August 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Anthony JE. Angew. Chem. Int. Ed. 2008; 47: 452
- 2 Zade SS, Bendikov M. Angew. Chem. Int. Ed. 2010; 49: 4012
- 3 Ye Q, Chi C. Chem. Mater. 2014; 26: 4046
- 4 Tönshoff C, Bettinger HF. Angew. Chem. Int. Ed. 2010; 49: 4125
- 5 Kaur I, Jazdzyk M, Stein NN, Prusevich P, Miller GP. J. Am. Chem. Soc. 2010; 132: 1261
- 6 Purushothaman B, Bruzek M, Parkin SR, Miller A.-F, Anthony JE. Angew. Chem. Int. Ed. 2011; 50: 7013
- 7 Muralidharan S, Yates K. J. Chem. Soc., Chem. Commun. 1991; 250
- 8 Clar E. Tetrahedron 1961; 16: 113
- 9 Fabian J, Nakazumi H, Matsuoka M. Chem. Rev. 1992; 92: 1197
- 10 Qian G, Wang ZY. Chem. Asian J. 2010; 5: 1006
- 11 Reichardt C. Chem. Rev. 1994; 94: 2319
- 12 Shimizu A, Ishizaki Y, Horiuchi S, Hirose T, Matsuda K, Sato H, Yoshida J. J. Org. Chem. 2021; 86: 770
- 13 Phillips JP, Keown RW. J. Am. Chem. Soc. 1951; 73: 5483
- 14 Krapcho AP, Gilmor TP. J. Heterocycl. Chem. 1998; 35: 669
- 15 Metzger A, Schade MA, Manolikakes G, Knochel P. Chem. Asian J. 2008; 3: 1678
- 16 Reichardt C. Chem. Soc. Rev. 1992; 21: 147
- 17 Kruszewski J, Krygowski TM. Tetrahedron Lett. 1972; 3839
- 18 Krygowski TM. J. Chem. Inf. Model. 1993; 33: 70
- 19 Schleyer P. vR, Maerker C, Dransfeld A, Jiao H, van Eikema Hommes NJ. R. J. Am. Chem. Soc. 1996; 118: 6317
- 20 Chen Z, Wannere CS, Corminboeuf C, Puchta R, Schleyer P. vR. Chem. Rev. 2005; 105: 3842
- 21 Herges R, Geuenich D. J. Phys. Chem. A 2001; 105: 3214
- 22 Geuenich D, Hess K, Köhler F, Herges R. Chem. Rev. 2005; 105: 3758
- 23 Counsell RE, Desai P, Ide A, Kulkarni PG, Weinhold PA, Rethy VB. J. Med. Chem. 1971; 14: 789
- 24 Villani FJ, King MS. Org. Synth. 1957; 37: 6