Issue 20, 2023

Predictable incorporation of nitrogen into carbon dots: insights from pinacol rearrangement and iminium ion cyclization

Abstract

Nitrogen-doped carbon dots (CDs) have attracted considerable attention across various research areas and applications due to their enhanced optical properties and photostability. However, the mechanism of nitrogen incorporation in CDs remains elusive, hampering the precise control over nitrogen-incorporated structures and the investigation of the effects of nitrogen on the electronic structure and optical properties of CDs. In this study, we employed a rational design approach, utilizing glucosamine and ethylene glycol as the carbon source and co-reagent, respectively, to synthesize N-doped CDs. Our synthesis strategy involved pinacol rearrangement and iminium ion cyclization reactions, enabling the reliable formation of N-doped CDs. Notably, the resulting CDs exhibited distinctive emissive states attributed to heteroatomic defect structures, including oxygenic and nitrogenic polycyclic aromatic hydrocarbons. To gain further insights into their energy levels and electronic transitions, we conducted comprehensive investigations, employing extended Hückel calculations and pump-probe spectroscopy. The synthesized CDs displayed great promise as bioimaging and photodynamic therapy agents, highlighting their potential for biomedical applications. Moreover, our study significantly contributes valuable insights into the rational design of N-doped CDs with controllable chemical and electronic structures, thereby paving the way for advancements in their diverse range of applications.

Graphical abstract: Predictable incorporation of nitrogen into carbon dots: insights from pinacol rearrangement and iminium ion cyclization

Supplementary files

Article information

Article type
Paper
Submitted
24 Jūl. 2023
Accepted
19 Sept. 2023
First published
21 Sept. 2023
This article is Open Access
Creative Commons BY-NC license

Nanoscale Adv., 2023,5, 5613-5626

Predictable incorporation of nitrogen into carbon dots: insights from pinacol rearrangement and iminium ion cyclization

S. Cho, C. Jung, D. Lee, Y. Byun, H. Kim, H. Han, J. Kim and W. Kwon, Nanoscale Adv., 2023, 5, 5613 DOI: 10.1039/D3NA00550J

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