Issue 42, 2021

Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core

Abstract

Nitroaromatics seldom fluoresce. The importance of electron-deficient (n-type) conjugates, however, has inspired a number of strategies for suppressing the emission-quenching effects of the strongly electron-withdrawing nitro group. Here, we demonstrate how such strategies yield fluorescent nitroaryl derivatives of dipyrrolonaphthyridinedione (DPND). Nitro groups near the DPND core quench its fluorescence. Conversely, nitro groups placed farther from the core allow some of the highest fluorescence quantum yields ever recorded for nitroaromatics. This strategy of preventing the known processes that compete with photoemission, however, leads to the emergence of unprecedented alternative mechanisms for fluorescence quenching, involving transitions to dark nπ* singlet states and aborted photochemistry. Forming nπ* triplet states from ππ* singlets is a classical pathway for fluorescence quenching. In nitro-DPNDs, however, these ππ* and nπ* excited states are both singlets, and they are common for nitroaryl conjugates. Understanding the excited-state dynamics of such nitroaromatics is crucial for designing strongly fluorescent electron-deficient conjugates.

Graphical abstract: Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core

Supplementary files

Article information

Article type
Edge Article
Submitted
06 7月 2021
Accepted
05 9月 2021
First published
29 9月 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 14039-14049

Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core

B. Sadowski, M. Kaliszewska, Y. M. Poronik, M. Czichy, P. Janasik, M. Banasiewicz, D. Mierzwa, W. Gadomski, T. D. Lohrey, J. A. Clark, M. Łapkowski, B. Kozankiewicz, V. I. Vullev, A. L. Sobolewski, P. Piatkowski and D. T. Gryko, Chem. Sci., 2021, 12, 14039 DOI: 10.1039/D1SC03670J

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