Synthesis of a Highly Twisted Dibenzo[g,p]chrysene
Conference Year
January 2019
Abstract
Polycyclic aromatic hydrocarbons that distort from planarity due to the presence of sterically bulky substituents or overlapping -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.
Primary Faculty Mentor Name
Adam C. Whalley
Status
Graduate
Student College
College of Arts and Sciences
Program/Major
Chemistry
Primary Research Category
Engineering & Physical Sciences
Synthesis of a Highly Twisted Dibenzo[g,p]chrysene
Polycyclic aromatic hydrocarbons that distort from planarity due to the presence of sterically bulky substituents or overlapping -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.