Dibenzopentalene-based conjugated nanohoops

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The goals of the proposed research are the synthesis and investigation of conjugated nanohoops, containing dibenzo[a,e]pentalene (DBP) units. As a non-alternant hydrocarbon with antiaromatic character, DBP is a low band-gap, ambipolar semiconductor, and conjugated DBP-based nanohoops are anticipated to possess intriguing properties. Three types of conjugated DBP-based nanohoops are proposed, for which preliminary investigations prove their syntheses to be feasible. Based on the inherent chirality of bent DBP units, chiral nanohoops will also be targeted. The structures and optoelectronic properties of the DBP-based nanohoops will be investigated using spectroscopic and electrochemical techniques as well as X-ray crystallography, accompanied by (TD)DFT calculations. Of particular interest is the effect of the bending on the antiaromaticity and frontier orbital energy levels of the DBP units as well as the extent of cyclic conjugation.