Utilization of K-region oxidation for the synthesis of functional materials

Walsh, Joshua C. (2016) Utilization of K-region oxidation for the synthesis of functional materials. Masters thesis, Memorial University of Newfoundland.

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Abstract

Pyrene with its long fluorescence lifetime, large Stokes shift and proclivity towards excimer formation has become the gold standard in the sensing of microenvironments using fluorescence spectroscopy. Derivatives of pyrene find applications in a broad range of fields. However, the design of more complex systems is hampered by the lack of selectivity one encounters when working with pyrene. Alkylation, halogenation and nitration produce practically inseparable isomers. Methods that desymmetrize pyrene are currently of high value. Known methods have recently been improved and applied to a number of systems within the Bodwell group. The optimization of a K-region oxidation reaction and utilization of desymmetrized pyrene in the synthesis of redox-active molecules and progress towards a 2,7-pyrenylene-ethynylene macrocycle is investigated in this thesis work. References [1] R. Rieger, K. Müllen, J. Phys. Org. Chem., 2010, 23, 315-325. [2] J. Andréasson, U. Pischel, Chem. Soc. Rev., 2015, 44, 1053-1069. [3] P. Conlon, C. J. Yang, Y. Wu, Y. Chen, K. Martinez, Y. Kim, N. Stevens, A. A. Marti, S. Jockusch, N. J. Turro, W. Tan, J. Am. Chem. Soc., 2008, 130, 336-342.

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