Chirality is a fascinating phenomenon for recent electrochemistry and materials research, allowing for the preparation of detection platforms based on analyte enantiodiscrimination and the development of advanced chiroptical devices and chiral electrodes. In this Viewpoint, we highlight new directions in the field of chiral helical polyaromatic molecules (mainly helicenes) that are useful for the preparation of optically and redox-active polymers and/or self-assembled thin layers, nanostructures and functional electrode surfaces. Instead of the previously reported chiral materials prepared by molecular imprinting, a concept based on the preparation of inherently chiral helicene-based materials with (opto)electrochemical applicability is presented. A short overview of well-established electrochemical methods for the research of chiral molecules is also outlined.

Department of Medical Chemistry and Biochemistry Faculty of Medicine and Dentistry Palacky University Hnevotinska 3 77515 Olomouc Czech Republic

Institute of Chemical Process Fundamentals Czech Academy of Sciences Rozvojova 135 16502 Prague 6 Czech Republic

Institute of Chemistry Masaryk University Kamenice 5 72500 Brno Czech Republic

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S. Ravichandran, V. K. Subramani, K. K. Kim, Biophys. Rev. Lett. 2019, 11, 383-387.

S. Sek, J. Vacek, V. Dorcak, Curr. Opin. Electrochem. 2019, 14, 166-172.

S. H. Reisberg, Y. Gao, A. S. Walker, E. J. N. Helfrich, J. Clardy, P. S. Baran, Science 2020, 367, 458-463.

J. R. Brandt, F. Salerno, M. J. Fuchter, Nat. Rev. Chem. 2017, 1, 0045.

M. Trojanowicz, Electrochem. Commun. 2014, 38, 47-52.

R. R. Gataullin, Russ. J. Org. Chem. 2019, 55, 1247-1274.

B. F. Watkins, J. R. Behling, E. Kariv, L. L. Miller, J. Am. Chem. Soc. 1975, 97, 3549-3550.

Z. Li, Z. Mo, S. Meng, H. Gao, X. Niu, R. Guo, Anal. Methods 2016, 8, 8134-8140.

W. Ma, L. Xu, L. Wang, C. Xu, H. Kuang, Adv. Funct. Mater. 2019, 29.

D. Mandler, Curr. Opin. Electrochem. 2018, 7, 42-47.

M. Kaniewska, T. Sikora, R. Kataky, M. Trojanowicz, J. Biochem. Biophys. Methods 2008, 70, 1261-1267.

V. Mirceski, F. Quentel, M. L′Her, Electrochem. Commun. 2009, 11, 1262-1264.

D. W. M. Arrigan, G. Herzog, Curr. Opin. Electrochem. 2017, 1, 66-72.

B. B. Prasad, M. P. Tiwari, R. Madhuri, P. S. Sharma, J. Chromatogr. B 2011, 879, 364-370.

S. Lalitha, A. Sampath Kumar, K. J. Stine, D. F. Covey, J. Supramol. Chem. 2001, 1, 53-61.

P. L. Rose, N. G. Harvey, E. M. Arnett, Adv. Phys. Org. Chem. 1993, 28, 45-138.

F. Pop, N. Zigon, N. Avarvari, Chem. Rev. 2019, 119, 8435-8478.

Y. Wang, J. Zhou, Q. Han, Q. Chen, L. Guo, Y. Fu, Electroanalysis 2012, 24, 1561-1566.

C. Wattanakit, A. Kuhn, Chem. Eur. J. 2020, 26, 2993-3003.

T. Yutthalekha, C. Wattanakit, V. Lapeyre, S. Nokbin, C. Warakulwit, J. Limtrakul, A. Kuhn, Nat. Commun. 2016, 7.

K. Dhbaibi, L. Favereau, J. Crassous, Chem. Rev. 2019, 119, 8846-8953.

H. Hopf, Chem. Rec. 2014, 14, 979-1000.

J. Hrbac, J. Storch, V. Halouzka, V. Cirkva, P. Matejka, J. Vacek, RSC Adv. 2014, 4, 46102-46105.

V. Halouzka, J. Hrbac, D. Jirovsky, D. Riman, P. Jakubec, Z. Bartosova, V. Masek, P. Mojzes, J. Vacek, Curr. Anal. Chem. 2013, 9, 305-311.

J. Hrbac, T. Strasak, L. Fekete, V. Ladanyi, J. Pokorny, J. Bulir, M. Krbal, J. Zadny, J. Storch, J. Vacek, ChemElectroChem 2017, 4, 3047-3052.

J. Vacek, J. Hrbac, T. Strasak, V. Cirkva, J. Sykora, L. Fekete, J. Pokorny, J. Bulir, M. Hromadova, J. Crassous, J. Storch, ChemElectroChem 2018, 5, 2080-2088.

J. Hrbac, V. Pavelka, J. Crassous, J. Zadny, L. Fekete, J. Pokorny, P. Vanysek, J. Storch, J. Vacek, Electrochem. Commun. 2020, 113, 106689.

S. Arnaboldi, S. Cauteruccio, S. Grecchi, T. Benincori, M. Marcaccio, A. O. Biroli, G. Longhi, E. Licandro, P. R. Mussini, Chem. Sci. 2019, 10, 1539-1548.

J. Storch, J. Zadny, T. Strasak, M. Kubala, J. Sykora, M. Dusek, V. Cirkva, P. Matejka, M. Krbal, J. Vacek, Chem. Eur. J. 2015, 21, 2343-2347.

Y. Yang, R. C. Da Costa, M. J. Fuchter, A. J. Campbell, Nature Photon. 2013, 7, 634-638.

V. Kolivoska, J. Sebera, L. Severa, G. Meszaros, R. Sokolova, J. Gasior, J. Kocabova, J. M. Hamill, L. Pospisil, M. Hromadova, ChemElectroChem 2019, 6, 5856-5863.

C. Shen, M. Srebro-Hooper, T. Weymuth, F. Krausbeck, J. T. L. Navarrete, F. J. Ramirez, B. Nieto-Ortega, J. Casado, M. Reiher, J. Autschbach, J. Crassous, Chem. Eur. J. 2018, 24, 15067-15079.

L. Pospisil, L. Bednarova, P. Stepanek, P. Slavicek, J. Vavra, M. Hromadova, H. Dlouha, J. Tarabek, F. Teply, J. Am. Chem. Soc. 2014, 136, 10826-10829.

K. H. Ernst, Acc. Chem. Res. 2016, 49, 1182-1190.

V. Kiran, S. P. Mathew, S. R. Cohen, I. H. Delgado, J. Lacour, R. Naaman, Adv. Mater. 2016, 28, 1957-1962.

J. Storch, K. Kalikova, E. Tesarova, V. Maier, J. Vacek, J. Chromatogr. A 2016, 1476, 130-134.

V. N. Khose, M. Hasan, S. C. Khot, S. M. Mobin, V. Borovkov, A. V. Karnik, J. Org. Chem. 2020, 85, 1847-1860.

F. Zinna, S. Voci, L. Arrico, E. Brun, A. Homberg, L. Bouffier, T. Funaioli, J. Lacour, N. Sojic, L. D Bari, Angew. Chem. Int. Ed. 2018, 58, 6952-6956.

I. Mogi, R. Morimoto, R. Aogaki, K. Watanabe, Sci. Rep. 2013, 3, 5.

A. Kumar, E. Capua, K. Vankayala, C. Fontanesi, R. Naaman, Angew. Chem. Int. Ed. 2017, 56, 14587-14590;

Angew. Chem. 2017, 129, 14779-14782.

P. C. Mondal, C. Fontanesi, D. H. Waldeck, R. Naaman, Acc. Chem. Res. 2016, 49, 2560-2568.

A. Kumar, P. C. Mondal, C. Fontanesi, Magnetochemistry 2018, 4, 4030036.

T. S. Metzger, S. Mishra, B. P. Bloom, N. Goren, A. Neubauer, G. Shmul, J. M. Wei, S. Yochelis, F. Tassinari, C. Fontanesi, D. H. Waldeck, Y. Paltiel, R. Naaman, Angew. Chem. Int. Ed. 2020, 59, 1653-1658.

R. Naaman, Y. Paltiel, D. H. Waldeck, Nat. Rev. Chem. 2019, 3, 250-260.

S. H. Yang, Appl. Phys. Lett. 2020, 116, 4.

L. Huang, Y. Li, Q. Lin, B. Lou, Y. Chen, Amino Acids 2019, 50, 1549-1556.

C. Wattanakit, T. Yutthalekha, S. Asssavapanumat, V. Lapeyre, A. Kuhn, Nat. Commun. 2017, 8.

S. K. Singh, A. W. Savoy, J. Mol. Liq. 2020, 297.

S. Grecchi, S. Arnaboldi, M. Korb, R. Cirilli, S. Araneo, V. Guglielmi, G. Tomboni, M. Magni, T. Benincori, H. Lang, P. R. Mussini, ChemElectroChem 2020, DOI: 10.1002/celc.202000657.

L. Jia, X. Liu, A. A. Zhang, T. Wang, Y. Hua, H. Li, L. Liu, Chem. Commun. 2020, 56, 1737-1740.

Lipid-based liquid crystalline materials in electrochemical sensing and nanocarrier technology