Supramolecular Ordering in Oligothiophene−Fullerene Monolayers

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• 作者：Jennifer M. MacLeod ; Oleksandr Ivasenko ; Chaoying Fu ; Tyler Taerum ; Federico Rosei ; Dmitrii F. Perepichka
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：November 25, 2009
• 年：2009
• 卷：131
• 期：46
• 页码：16844-16850
• 全文大小：387K
• 年卷期：v.131,no.46(November 25, 2009)
• ISSN：1520-5126

文摘

Scanning tunneling microscopy (STM) of monolayers comprising oligothiophene and fullerene molecular semiconductors reveals details of their molecular-scale phase separation and ordering with potential implications for the design of organic electronic devices, in particular future bulk heterojunction solar cells. Prochiral terthienobenzenetricarboxylic acid (TTBTA) self-assembles at the solution/graphite interface into either a porous chicken wire network linked by dimeric hydrogen bonding associations of COOH groups (R₂²(8)) or a close-packed network linked in a novel hexameric hydrogen bonding motif (R₆⁶(24)). Analysis of high-resolution STM images shows that the chicken wire phase is racemically mixed, whereas the close-packed phase is enantiomerically pure. The cavities of the chicken wire structure can efficiently host C₆₀ molecules, which form ordered domains with either one, two, or three fullerenes per cavity. The observed monodisperse filling and long-range co-alignment of fullerenes is described in terms of a combination of an electrostatic effect and the commensurability between the graphite and molecular network, which leads to differentiation of otherwise identical adsorption sites in the pores.