Functional Carbazole‐Fullerene Complexes: A New Perspective of Carbazoles Acting as Nano‐Octopus to Capture Globular Fullerenes

Abstract

Fullerene host-guest constructs have attracted increasing attention owing to their molecular-level hybrid arrangements. However, the usage of simple carbazolic derivatives to bind with fullerenes is rare. In this research, three novel carbazolic derivatives, containing a tunable bridging linker and carbazole units for the capturing of fullerenes, are rationally designed. Unlike the general concave-convex interactions, fullerenes could interact with the planar carbazole subunits to form 2-dimensional hexagonal/ quadrilateral cocrystals with alternating stacking patterns of 1 : 1 or 1 : 2 stoichiometry, as well as the controllable fullerene packing modes. At the meanwhile, good electron-transporting performances and significant photovoltaic effects were realized when a continuous C 60••• C 60 interaction channel existed. The results indicate that the introduction of such carbazolic system into fullerene receptor would provide new insights into novel fullerene host-guest architectures for versatile applications.

From Induced-Fit Assemblies to Ternary Inclusion Complexes with Fullerenes in Corannulene-Based Molecular Tweezers

“…For the above reasons, this design then allows us to determine the effect of the bridgehead group and the differential behavior between C 60 and C 70 recognition, if any. We provide a variety of motifs usually encountered in optoelectronic materials − from strong donors to typical acceptors. From a simplistic point of view, considering exclusively the electronic donor–acceptor properties of hosts and guests and chemical intuition, the best association with fullerenes would be found in N -tolyl carbazole 16 , whereas the worst one in ylidenmalononitrile 11-C­(CN) 2 .…”

Fullerene C70/porphyrin hybrid nanoarchitectures: single-cocrystal nanoribbons with ambipolar charge transport properties

“…There are many studies in the literature on D–A cocrystal-based FETs reporting n-type, p-type, or ambipolar characteristics; 17–21 however, their characteristics and charge transport mechanisms have not yet been fully understood. In order to understand the mechanism of the ambipolar charge transport properties, a comparison of C 70 /3,5-TPP cocrystals observed in the present study with our earlier report on C 60 /3,5-TPP cocrystals 17 that showed only n-type behavior may be useful.…”

“…In contrast, the cocrystallization process can be conducted by simple mixing of two (or more) molecules and does not involve any complex synthesis protocols. Notably, not all D-A cocrystal-based FETs exhibit ambipolar transport properties, some exhibit the unipolar ones, such as n-type [17][18][19][20] or p-type. 21 Therefore, further research is necessary to understand these characteristics in detail.…”