Defective Nanographenes Containing Seven-Five-Seven (7-5-7)-Membered Rings

Fei Y, Fu Y, Bai X, Du L, Li Z, Komber H, Low KH, Zhou S, Phillips DL, Feng X, Liu J (2021)

Publication Type: Journal article

Publication year: 2021

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 143

Pages Range: 2353-2360

Journal Issue: 5

DOI: 10.1021/jacs.0c12116

Abstract

Defects have been observed in graphene and are expected to play a key role in its optical, electronic, and magnetic properties. However, because most of the studies focused on the structural characterization, the implications of topological defects on the physicochemical properties of graphene remain poorly understood. Here, we demonstrate a bottom-up synthesis of three novel nanographenes (1-3) with well-defined defects in which seven-five-seven (7-5-7)-membered rings were introduced to their sp2 carbon frameworks. From the X-ray crystallographic analysis, compound 1 adopts a nearly planar structure. Compound 2, with an additional five-membered ring compared to 1, possesses a slightly saddle-shaped geometry. Compound 3, which can be regarded as the "head-to-head"fusion of 1 with two bonds, features two saddles connected together. The resultant defective nanographenes 1-3 were well-investigated by UV-vis absorption, cyclic voltammetry, and time-resolved absorption spectra and further corroborated by density functional theory (DFT) calculations. Detailed experimental and theoretical investigations elucidate that these three nanographenes 1-3 exhibit an anti-aromatic character in their ground states and display a high stability under ambient conditions, which contrast with the reported unstable biradicaloid nanographenes that contain heptagons. Our work reported herein offers insights into the understanding of structure-related properties and enables the control of the electronic structures of expanded nanographenes with atomically precise defects.

Involved external institutions

University of Hong Kong (HKU) / 香港大學 HK Hong Kong (HK) Helmholtz-Zentrum Dresden-Rossendorf (HZDR) DE Germany (DE) Technische Universität Dresden DE Germany (DE) Leibniz-Institut für Polymerforschung Dresden e. V. DE Germany (DE)

How to cite

APA:

Fei, Y., Fu, Y., Bai, X., Du, L., Li, Z., Komber, H.,... Liu, J. (2021). Defective Nanographenes Containing Seven-Five-Seven (7-5-7)-Membered Rings. Journal of the American Chemical Society, 143(5), 2353-2360. https://doi.org/10.1021/jacs.0c12116

MLA:

Fei, Yiyang, et al. "Defective Nanographenes Containing Seven-Five-Seven (7-5-7)-Membered Rings." Journal of the American Chemical Society 143.5 (2021): 2353-2360.

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