Beilstein J. Org. Chem.2023,19, 736–751, doi:10.3762/bjoc.19.54
].
When three HBCs were fused together linearly, the graphene nanoribbons would be constructed. Wang [46] and Campaña [52] groups separately reported the synthesis of graphene nanoribbon 73 (Scheme 8), which contains four [5]carbohelicenes due to bulky tert-butyl groups as lateral chains. In brief
(M)-110 at 684 nm were up to 4.50 × 10−2 and 4.22 × 10−2, respectively. Wang and co-workers reported a chiral graphene nanoribbon 115 (Scheme 12) by linearly fusing four HBS units in a helical manner [46]. The synthesis started by construction of a HBC-dimer 111. para-Iodization of 111 gave compound
112 in a 91% yield. Scholl oxidation of 112, and then Sonogashira coupling of 113 yielded the bisalkyne, which was ready for a second Diels−Alder reaction to give precursor 114. Through dehydrocyclization induced by DDQ and TfOH, precursor 114 was transformed to nanoribbon 115 in a 5% yield. This
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Graphical Abstract
Scheme 1:
Construction of HBC by Scholl reaction from hexaphenylbenzene.
Beilstein J. Org. Chem.2015,11, 2343–2349, doi:10.3762/bjoc.11.255
driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π–π stacking interactions. The electronic conductivity of the T1 and T2 films was tested by a four-probe method.
Keywords: hydrogen bond; nanoribbon; self-assembly; tetrathiafulvalene; urethane; Introduction
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Graphical Abstract
Figure 1:
Molecular structure of TTF derivatives T1 and T2.