E. C. RÜDIGER, M. PORZ, M. SCHAFFROTH, F. ROMINGER, U. H. F. BUNZ* (RUPRECHT-
Ca t e g o r y
KARLS-UNIVERSITÄT, HEIDELBERG, GERMANY)
Synthesis of
Materials and
Unnatural Products
Synthesis of Soluble, Alkyne-Substituted Trideca- and Hexadeca-Starphenes
Chem. Eur. J. 2014, 20, 12725–12728.
A Starphene is Born: Largest and Most
Soluble to Date
Ke y w o rd s
electronic materials
starphenes
Yamamoto coupling
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Significance: These are the largest reported star-
Comment: The starphenes were assembled via a
phenes to date. Starphenes have garnered attention as organic electronic materials, but previously
synthesized versions were extremely poorly soluble and therefore difficult to characterize. The reported structures are more soluble, enabeling
NMR and crystallographic data, confirming their
structure and packing order into potentially conductive configurations. UV/Vis data indicate that
these starphenes have band gaps of 1.8–2.3 eV.
Yamamoto coupling with reasonably good yield
(≥50% after column chromatography), with crystallographic confirmation of star, rather than linear,
structure required. It is also notable that the smaller starphene (left) packed into the predicted 1-D
stack, while the larger (right) formed pairs of
stacked starphenes that then ordered themselves
laterally, which had never before been observed.
SYNFACTS Contributors: Timothy M. Swager, Elizabeth S. Sterner
Synfacts 0312014, 10(11), 1147 Published online: 20.10.20141861-19581861-194X
DOI: 10.1055/s-0034-1379285; Reg-No.: S10314SF
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