Structure and photophysical properties of furoquinoline aza-helicenes: Fluorescence enhancement by protonation

Structure and photophysical properties of furoquinoline aza-helicenes: Fluorescence enhancement by protonation Научная публикация

Журнал

Dyes and Pigments
ISSN: 1873-3743 , E-ISSN: 0143-7208

Вых. Данные

Год: 2024, Том: 225, Номер статьи : 112032, Страниц : DOI: 10.1016/j.dyepig.2024.112032

Авторы

Balakhonov R.Y. ¹ , Gaeva E.B. ² , Mekeda I.S. ¹ , Dolotov R.A. ¹ , Metelitsa A.V. ² , Shirinian V.Z. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991, Moscow, Russian Federation
2	Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Avenue, Rostov on Don, 344090, Russian Federation

In recent years, the introduction of one or more heteroaromatic rings into a polyaromatic backbone has attracted growing interest as it allows significant control over optical, electronic and supramolecular characteristics. Polyheteroaromatic compounds are potential optoelectronic conjugate materials due to their photo- and electrochemical properties. This work describes the structure and photophysical properties of the first representatives of azaoxahelicenes of the furoquinoline series, synthesized from readily available starting compounds. Using X-ray diffraction analysis and DFT calculations, it was established that furan-fused aza [5]helicenes, unlike their carbon analogues, do not undergo Mallory-type photocyclization due to an increase in the distance between the terminal carbon atoms, which determines their greater resistance to UV light. A study of the acidochromic properties of the obtained compounds showed that protonation with trifluoroacetic acid (TFA) leads to an increase in the fluorescence intensity of most fluorophores. The best fluorescence enhancement was obtained for a fluorophore containing a methoxy substituent in the peripheral phenyl moiety, with a 10-fold increase in quantum yield. The introduction of a furoquinoline residue into the helicene skeleton leads to an improvement in fluorescent properties, as well as the possibility of their modulation by acidic agents. In the future, the first representatives of azaoxahelicenes of the naphthofuroquinoline series will be used to design new materials for optoelectronics and study their performance properties.

Balakhonov R.Y. , Gaeva E.B. , Mekeda I.S. , Dolotov R.A. , Metelitsa A.V. , Shirinian V.Z.
Structure and photophysical properties of furoquinoline aza-helicenes: Fluorescence enhancement by protonation
Dyes and Pigments. 2024. V.225. 112032 . DOI: 10.1016/j.dyepig.2024.112032 WOS Scopus OpenAlex

Web of science:	WOS:001204379300001
Scopus:	2-s2.0-85186961494
OpenAlex:	W4392345068

БД	Цитирований
OpenAlex	3
Scopus	4