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Helquats: A Facile, Modular, Scalable Route to Novel Helical Dications

Authors

  • Louis Adriaenssens Dr.,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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  • Lukáš Severa,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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  • Tereza Šálová,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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  • Ivana Císařová,

    1. Department of Inorganic Chemistry, Charles University, Hlavova 2030, 128 40 Prague (Czech Republic)
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  • Radek Pohl Dr.,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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  • David Šaman Dr.,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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  • Silvia V. Rocha Dr.,

    1. Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
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  • Nathaniel S. Finney Dr.,

    1. Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
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  • Lubomír Pospíšil Dr.,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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  • Petr Slavíček Dr.,

    1. Department of Physical Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague (Czech Republic)
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  • Filip Teplý Dr.

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6 (Czech Republic), Fax: (+420) 220-183-578
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Abstract

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As easy as one, two, three: Relying on a facile [2+2+2]-cycloisomerization strategy, we have developed a robust three-step synthetic entry into a novel family of helical extended diquats (helquats). The key metal-catalyzed step proceeds in water under aerobic conditions to produce a water-soluble, blue fluorophore (picture; TfO=triflate). The electrochemical manifold of the parent helquat features two reversible one-electron reduction steps.

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