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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/00216208:11310/22:10444788

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA20-19353S" target="_blank" >GA20-19353S: Příprava a charakterizace hybridních plazmonických nanostruktur se silnou chirální odezvou</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

87

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

17

Strana od-do

7150-7166

Kód UT WoS článku

000809765000014

EID výsledku v databázi Scopus

2-s2.0-85131082446