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Lee, Ji-Eun,Stepanenko, Vladimir,Yang, Jaesung,Yoo, Hyejin,Schlosser, Felix,Bellinger, Daniel,Engels, Bernd,Scheblykin, Ivan G.,Wü,rthner, Frank,Kim, Dongho American Chemical Society 2013 ACS NANO Vol.7 No.6
<P>Properties of a series of acetylene-linked perylene bisimide (PBI) macrocycles with different ring size composed of three to six PBI dyes were investigated by atomic force microscopy (AFM) and single-molecule fluorescence spectroscopy in a condensed phase. It was demonstrated that the structures of PBI cyclic arrays (C<I>N</I>s, <I>N</I> = 3, 4, 5, and 6) become distorted with increasing the ring size through molecular dynamics (MD) simulations (PM6-DH2 method) and AFM height images of C<I>N</I>s on highly ordered pyrolytic graphite (HOPG) surface. The MD simulations showed that only <B>C5</B> and <B>C6</B> rings are highly flexible molecules whose planarization goes along with a significant energetic penalty. Accordingly, both molecules did not show ordered adlayers on a HOPG surface. In contrast, <B>C3</B> and <B>C4</B> are far more rigid molecules leading to well-ordered hexagonal (<B>C3</B>) and rectangular (<B>C4</B>) 2D lattices. At the single-molecule level, we showed that the fluorescence properties of single C<I>N</I>s are affected by the structural changes. The fluorescence lifetimes of C<I>N</I>s became shorter and their distributions became broader due to the structural distortions with increasing the ring size. Furthermore, the C<I>N</I>s of smaller ring size exhibit a higher photostability and an efficient excitation energy transfer (EET) due to the more well-defined and planar structures compared to the larger C<I>N</I>s. Consequently, these observations provide evidence that not only PBI macrocycles are promising candidates for artificial light-harvesting systems, but also the photophysical properties of C<I>N</I>s are strongly related to the structural rigidity of C<I>N</I>s.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/ancac3/2013/ancac3.2013.7.issue-6/nn400616u/production/images/medium/nn-2013-00616u_0012.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/nn400616u'>ACS Electronic Supporting Info</A></P>