Chad Junkermeier1,George Psofogiannakis2,Ricardo Paupitz3
University of Hawaii Maui College1,University of Ottawa2,Universidade Estadual Paulista3
Chad Junkermeier1,George Psofogiannakis2,Ricardo Paupitz3
University of Hawaii Maui College1,University of Ottawa2,Universidade Estadual Paulista3
[N]-carbophenes (carbophenes) are a novel class of two-dimensional covalent organic framework, based on linear [N]-phenylenes, the simplest of which may have been recently synthesized.[1] Tight-binding density functional theory was used to determine the ground-state configurations of single layers, bilayers, and bulk carbophenes.[2] Carbophenes have formation energies per carbon atom similar to that of graphenylene. The similarity of formation energies between graphenylene and carbophenes suggests that when trying to synthesize one, the other may also be synthesized. The formation energies could explain why the first reported synthesis of graphenylene also indicated that they may have inadvertently synthesized 3-carbophene. The projected density of states demonstrates that the anti-aromatic nature of the cyclobutene units plays a direct role in creating bands around the Fermi level. Thus, carbophenes are promising candidates for investigations aiming to<br/>reveal the nature of aromatic bonds.<br/>This presentation focuses on replacing the hydrogen terminating agents of pristine carbophenes with the functional groups OH, NO<sub>2</sub>, NH<sub>2</sub>, COOH, and CO. At all levels of replacement, the functional groups studied are energetically favorable when compared to hydrogen. The band gaps of functionalized carbophenes are dependent on the type of carbophene, the type of functional group, and the degree of coverage, leading to the ability to tune the band gap over a range of ~2 eV. Due to the regular pore structures of single-layer carbophenes, the favorable AA stacking of multi-layers, and the ability to highly functionalize the pores, carbophenes are exciting materials for applications in nanofluidics, sensors, and gas (liquid) separation.<br/>References<br/>1. Du Q-S, Tang P-D, Huang H-L, Du F-L, Huang K, Xie N-Z, Long S-Y, Li Y-M, Qiu J-S, Huang R-B (2017) A new type of two-dimensional carbon crystal prepared from 1,3,5-trihydroxybenzene. <i>Scientific Reports</i>, 7:40796. https://doi.org/10.1038/srep40796<br/>2. Junkermeier CE, Luben JP, Paupitz R (2019) N-Carbophenes: Two-dimensional covalent organic frameworks derived from linear N-phenylenes. <i>Materials Research Express</i>, 6(11):115103. https://doi.org/10.1088/2053-1591/ab4513