Synthesis of a Highly Twisted Dibenzo[g,p]chrysene
Dyer, Adam M
Dyer, Adam M
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Abstract
Polycyclic aromatic hydrocarbons that distort from planarity due to the presence of sterically bulky substituents or overlapping π-systems often exhibit interesting supramolecular and optoelectronic properties as a result of their strained structures. Of particular interest is dibenzo[g,p]chrysene, which exhibits two [4]helicene units joined through a central naphthalene moiety. In this presentation we will introduce the first derivative of this molecule that is functionalized at the 1 and 16 positions which we synthesized from the well-known [1-3]orthocyclophane macrocycle. The solid-state structure obtained from single crystal X-ray diffraction studies confirms an impressive 44° dihedral angle between the terminal C–C bonds of the central naphthalene unit – illustrating one of the most twisted hydrocarbons synthesized to date. Additional details describing the optoelectronic properties and the energy required for racemization of this chiral structure will also be presented.
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Date
2019-01-01
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Graduate
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Poster Presentation
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Chemistry
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College of Arts and Sciences
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Engineering & Physical Sciences