Previous research has demonstrated the versatility of supramolecular metallocages in a wide variety of applications. Fe8L6 metal-organic cages (L=tetraphenyliminopyridyl-porphyrin) have been shown to encapsulate large aromatic hydrocarbons such as C60 and coronene. We report the synthesis of two new guests for encapsulation within these host cages: pentahelicene (1, PH) and 2,4,6,8-tetracyanazulene (2, TCNA). Both are ideal candidates for encapsulation and binding studies. Pentahelicene is a large helical hydrocarbon with two chiral conformations. Because the Fe8L6 metallocage is itself chiral, PH may show preferential binding to either the right-handed or left-handed cage. TCNA has two cyano groups ideally situated to facilitate two-site binding within a Zn-porphyrin metallocube. This binding should alter the internal guest dynamics. The pentahelicene synthesis has so far proceeded to 7,8-dibromopentahelicene and remains to be dehalogenated. 6-Methylazulene has successfully been synthesized in 52% yield, and we will report on its cyanation.

Synthesis of pentahelicene and tetracyanoazulene: Two new aromatic guests for supramolecular metallocage encapsulation

255th National Meeting (2018)

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