Synthesis of Aza[n]helicenes (n = 4–7) via Photocyclodehydrochlorination of 1-Chloro-N-aryl-2-naphthamidesClick to copy article linkArticle link copied!
- Lubomír VáňaLubomír VáňaDepartment of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech RepublicMore by Lubomír Váňa
- Martin JakubecMartin JakubecDepartment of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech RepublicMore by Martin Jakubec
- Jan Sýkora*Jan Sýkora*E-mail: [email protected]Department of Analytical Chemistry, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech RepublicMore by Jan Sýkora
- Ivana CísařováIvana CísařováDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 40 Prague 2, Czech RepublicMore by Ivana Císařová
- Jaroslav ŽádnýJaroslav ŽádnýDepartment of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech RepublicMore by Jaroslav Žádný
- Jan StorchJan StorchDepartment of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech RepublicMore by Jan Storch
- Vladimír Církva*Vladimír Církva*E-mail: [email protected]Department of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech RepublicMore by Vladimír Církva
Abstract
A series of aza[n]helicenes (n = 4–7) was synthesized using a photocyclodehydrochlorination of 1-chloro-N-aryl-2-naphthamides as a general synthetic procedure introducing the nitrogen atom to the third ring of the helicene framework. The effect of the nitrogen presence in the helicene skeleton on the physicochemical properties of the prepared aza[n]helicenes was studied and compared to those of the parent carbo-analogues. The insertion of a nitrogen atom into the outer edge of the helicene molecule has a severe impact on certain physicochemical properties such as optical rotation, electrostatic potentials, and intermolecular interactions. On the other hand, some other properties such as UV/vis, fluorescence, and phosphorescence spectra remained almost unaffected when compared to the parent carbohelicenes. A nitrogen atom can be also used for further derivatization, which can lead to further modification of helicene properties, as manifested here in the fluorescence changes induced by protonation.
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