Synthesis of Aza[n]helicenes (n = 4–7) via Photocyclodehydrochlorination of 1-Chloro-N-aryl-2-naphthamides.

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F22%3A00557561" target="_blank" >RIV/67985858:_____/22:00557561 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/22:10444788
Result on the web
<a href="http://hdl.handle.net/11104/0331527" target="_blank" >http://hdl.handle.net/11104/0331527</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c00375" target="_blank" >10.1021/acs.joc.2c00375</a>

Result language
angličtina
Original language name
Synthesis of Aza[n]helicenes (n = 4–7) via Photocyclodehydrochlorination of 1-Chloro-N-aryl-2-naphthamides.
Original language description
A series of aza[n]helicenes (n = 4−7) was synthesized using a photocyclodehydrochlorination of 1-chloro-N-aryl-2-nnaphthamides 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.
Czech name
—
Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA20-19353S" target="_blank" >GA20-19353S: Preparation and characterization of hybrid plasmonic nanostructures with strong chiral response</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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