Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 14, Pages 5234-5243Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0706574
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A series of planar and twisted heteroaromatic quaterphenyl analogues containing BN ring linkages has been synthesized using primarily difunctional Lewis acidic diborabiphenyl moieties as molecular cores. Crystal structure analyses indicated the presence of large twist angles between adjacent aromatic rings in 1 and 3, which were also observed to possess nonfluorescent behavior due to a lack of molecular rigidity and insufficient BN character in the excited state. In contrast, the incorporation of one or two bridging ethylene groups between the adjacent rings (installed via an ethynyl cycloisomerization) was found to afford planar phenanthrene or pyrene moieties, which resulted in weak fluorescence behavior (Phi(F) = 0.02-0.16) for the n-Bu and Ph derivatives 5-12. Emission colors ranged from green (lambda(em) = 521 nm) to red (lambda(em) = 630 nm) and depended primarily on the conformation (2,2'- vs 4,4'-), the extent of chromophore conjugation (phenanthrene vs pyrene), and the type of exocyclic substituent present (n-Bu vs Ph). Communication between the two phenanthrene or pyrene moieties was observed in some cases, which was characterized by bathochromically shifted emission bands relative to that of monomeric phenanthrene or pyrene species. Unique excited-state dimer (excimer) fluorescence was observed for the 2,2'-isomer 8, which was characterized by broad, low-energy emission bands bathochromically shifted from that of the corresponding monomer.
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