The phane properties of anti-[2.2](1,4)biphenylenophane

Man Kit Leung*, M. Balaji Viswanath, Pi Tai Chou, Shih Chieh Pu, Hsin-Chieh Lin, Bih Yaw Jin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

(Chemical Equation Presented) anti-[2.2](1,4)Biphenylenophane (4) was synthesized from de Meijere's tetrabromo[2.2]paracyclophane (5) through a four-step reaction sequence. Although an average separation of 3.09 Å between the inner ring of the biphenylene units is normal for [2.2]paracyclophanes, a bond distance of 1.54 Å for the ethano C-C bridge at room temperature is shorter than usual. In addition, trimethylsilyl- substituted anti-[2.2](1,4)biphenylenophane 8 sublimes at 220°C under a pressure lower than 1 × 10-5 Torr without decomposition or thermal isomerization. The high thermal stability of 8 suggested that the ethano bridges of the biphenylenophanes are less strained than those of [2.2]paracyclophane. Bathochromic shifts are observed in their UV-vis absorption spectra. The phane state interactions of 4 and 8 were evidenced by the weak structureless fluorescent emission maximized at 537 and 550 nm in CH 2Cl2 along with longer relaxation lifetimes of 229 and 292 ps, respectively.

Original languageEnglish
Pages (from-to)3560-3568
Number of pages9
JournalJournal of Organic Chemistry
Volume70
Issue number9
DOIs
StatePublished - 29 Apr 2005

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