Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity

Krzysztof Durka , Mateusz Urban , Marek Dąbrowski , Piotr Jankowski , Tomasz Kliś , Sergiusz Luliński

Abstract

A series of isomeric boronated acridinium dyes were obtained by reactions of 10-(4′-octyloxyphenyl) functionalized 9(10H)-acridanone derivative with lithiated phenylboronic azaesters followed by aromatization with perchloric acid. The effect of the position of boronic group attached at ortho, meta, and para positions of the 9-phenyl ring on the photophysical properties was investigated. Conversion to related betaine trifluoroborato-substituted compounds was successfully performed, and the effect of this structural change on UV–vis absorption and fluorescence spectroscopy characteristics was established. Furthermore, cyclic voltammetry studies revealed that electrochemical behavior of cationic versus betaine structures is different in terms of redox potential values as well as stability. The theoretical calculations revealed a different scheme for molecular excitation processes in B(OH)2 versus BF3–-substituted compounds as charge transfer to acridinium core is observed from N-aryl or B-aryl moiety, respectively. Obtained compounds were active as photocatalysts in selected visible-light-promoted addition reactions to unsaturated substrates.
Author Krzysztof Durka (FC / DPC)
Krzysztof Durka,,
- Department Of Physical Chemistry
, Mateusz Urban (FC / DPC)
Mateusz Urban,,
- Department Of Physical Chemistry
, Marek Dąbrowski (FC / DPC)
Marek Dąbrowski,,
- Department Of Physical Chemistry
, Piotr Jankowski (FC / CofIC)
Piotr Jankowski,,
- Chair Of Inorganic Chemistry
, Tomasz Kliś (FC / DPC)
Tomasz Kliś,,
- Department Of Physical Chemistry
, Sergiusz Luliński (FC / DPC)
Sergiusz Luliński,,
- Department Of Physical Chemistry
Journal seriesACS Omega, ISSN 2470-1343, (N/A 70 pkt)
Issue year2019
Vol4
No2
Pages2482-2492
Publication size in sheets0.5
ASJC Classification16 Chemistry
DOIDOI:10.1021/acsomega.8b03290
URL https://pubs.acs.org/doi/10.1021/acsomega.8b03290
Languageen angielski
File
acsomega.8b03290.pdf 2.07 MB
Score (nominal)70
ScoreMinisterial score = 70.0, 16-09-2019, ArticleFromJournal
Publication indicators Scopus Citations = 1; WoS Citations = 1
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