Near‐Infrared Photoluminescence and Electrochemiluminescence from a Remarkably Simple Boron Difluoride Formazanate Dye

A boron difluoride formazanate dye that exhibits near‐infrared photoluminescence and electrochemiluminescence was produced via a straightforward two‐step synthesis. Examination of its solid‐state structure suggested that the N‐aryl substituents have significant quinoidal character, which narrows the...

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Bibliographic Details
Published in:Angewandte Chemie 2019-01, Vol.131 (4), p.1064-1068
Main Authors: Maar, Ryan R., Zhang, Ruizhong, Stephens, David G., Ding, Zhifeng, Gilroy, Joe B.
Format: Article
Language:English
Subjects:
Aromatic compounds
Boron
Chemistry
Developmental stages
Difluorides
Dyes
Electrochemiluminescence
Elektrochemie
Elektrochemilumineszenz
Energy gap
Formazanat-Liganden
Infrared imaging
Luminescence
Nahinfrarot-Photolumineszenz
Optoelectronics
Organische Farbstoffe
Oxidation
Photoluminescence
Photons
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Summary:A boron difluoride formazanate dye that exhibits near‐infrared photoluminescence and electrochemiluminescence was produced via a straightforward two‐step synthesis. Examination of its solid‐state structure suggested that the N‐aryl substituents have significant quinoidal character, which narrows the S1–S0 energy gap and leads to the unique optoelectronic properties observed. Cyclic voltammetry studies revealed two oxidation waves and two reduction waves that were electrochemically reversible. Electrochemiluminescence properties were examined in the presence of tri‐n‐propylamine, leading to maximum intensity at 910 nm, at least 85 nm (1132 cm−1) red‐shifted compared to all other organic dyes. This work sets the stage for the development of future generations of dyes for emerging applications, including single‐cell imaging, that require near‐infrared photoluminescence and electrochemiluminescence. Zwei Eigenschaften: Ein einfacher, über eine zweistufige Synthese zugänglicher Bordifluorid‐Formazanat‐Farbstoff weist Nahinfrarot‐Photolumineszenz und ‐Elektrochemilumineszenz auf. Die N‐Arylsubstituenten haben deutlich chinoiden Charakter, sodass sich die Energiedifferenz zwischen S1 und S0 verringert und einzigartige optoelektronische Eigenschaften auftreten.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201811144