Graphene-like Molecules Based on Tetraphenylethene
Oligomers: Synthesis, Characterization, and Applications
- Publication date
- Publisher
Abstract
Graphene-like
molecules were prepared by oxidative cyclodehydrogenation
of tetraphenylethene(TPE) oligomers using iron(III) chloride as the
catalyst under mild conditions. All the oxidized samples can be separated
effectively from the stepwise ring-closing reaction that highly related
to the reaction time. For example, the model compounds obtained from
the stepwise cyclization reaction show a regular red-shift in UV/vis
absorption and photoluminescence (PL) spectra. This result reveals
that the molecular conjugation length will extend with the stepwise
ring-closing reaction going on. Interestingly, we successfully obtained
a series of colorful luminogens with blue, cyan, and green emission
during this stepwise and accurate ring closing process. Cyclic voltammetry
measurements taken give the corresponding band gap, which supports
the results obtained from optical spectroscopy. For the strong intermolecular
interaction, our graphene molecules can self-assemble to form a red-colored
and hexagonal fiber. Furthermore, some molecules exhibit piezochromic
luminescence. The PL emission of the molecules before and after oxidation
can be dramatically quenched by picric acid through the electron transfer
and/or energy transfer mechanism, enabling them to function as chemosensors
for explosive detection. In addition, fluorescence cell imaging studies
proved their potential biological application