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1,3-Di(hetero)aryl-7-substituted pyrenes – an undiscovered area of important pyrene derivatives
Dawid Zych
1  Helmholtz Zentrum Berlin fur Materialen und Energie

10.3390/ecsoc-23-06470 (registering DOI)
Abstract:

Despite the pyrene derivatives have been covered extensively by scientists during the last years, many interesting properties and applications of pyrene derivatives have been presented, nowadays there are still areas of pyrenes’ chemistry that need to be fulfilled. Most of the described in literature pyrenes are 1,3,6,8-tetrasubstituted followed by 4,5,9,10-tetrasubstituted, 2,7-, and 1,6-, and 1,8-disubstituted pyrene derivatives. In the case of 1,3-di(hetero)aryl-7-substituted, there are only a few examples of derivatives containing at position 7 - tert-butyl group. In this work, the necessity of synthesis of 1,3-di(hetero)aryl-7-substituted pyrenes is presented based on the results of theoretical calculations by using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) by using Gaussian 09 program with B3LYP exchange-correlation functional and 6-31G** basis set. What is more, the synthetic routes with feasible reagents and conditions are presented. As the starting material, 1,3-dibromo-7-nitropyrene will be used which can be synthesized based on the literature method starting from commercially available pyrene. This compound will be used in the next steps in the synthesis of 1,3-disubstituted by (hetero)aryl groups pyrene derivatives which will be also substituted at position 7 by various groups. It will be possible by exchange nitro group at position 7 on amine group followed by a further exchange on bromine group. Properly selected substituents (the part of target molecules containing at positions 1 and 3 heteroaryl groups suitable for the coordination of metal ions) will allow also to determine the application of new pyrene derivatives as NCN-cyclometalating ligands with various d-block metals.

Keywords: pyrene derivatives; (hetero)aryl groups; DFT; TD-DFT; synthetic routes
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