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

Váňa, Lubomír; Jakubec, Martin; Sýkora, Jan; Císařová, I.; Žádný, Jaroslav; Storch, Jan; Církva, Vladimír

doi:https://dx.doi.org/10.1021/acs.joc.2c00375

Number of the records: 1

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

1.

SYSNO ASEP	0557561
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis of Aza[n]helicenes (n = 4–7) via Photocyclodehydrochlorination of 1-Chloro-N-aryl-2-naphthamides.
Author(s)	Váňa, Lubomír (UCHP-M) Jakubec, Martin (UCHP-M)_{RID, ORCID, SAI} Sýkora, Jan (UCHP-M)_{RID, ORCID, SAI} Císařová, I. (CZ) Žádný, Jaroslav (UCHP-M)_{RID, SAI, ORCID} Storch, Jan (UCHP-M)_{RID, ORCID, SAI} Církva, Vladimír (UCHP-M)_{RID, ORCID, SAI}
Source Title	Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263 Roč. 87, č. 11 (2022), s. 7150-7166
Number of pages	17 s.
Language	eng - English
Country	US - United States
Keywords	aromatic compounds ; photocyclization ; emission
OECD category	Organic chemistry
R&D Projects	GA20-19353S GA ČR - Czech Science Foundation (CSF)
Method of publishing	Open access with time embargo (04.06.2023)
Institutional support	UCHP-M - RVO:67985858
UT WOS	000809765000014
EID SCOPUS	85131082446
DOI	10.1021/acs.joc.2c00375
Annotation	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.
Workplace	Institute of Chemical Process Fundamentals
Contact	Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227
Year of Publishing	2023
Electronic address	http://hdl.handle.net/11104/0331527

Number of the records: 1