An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives |
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Authors: | Joshua J Pak Jaime L Mayo Endrit Shurdha |
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Institution: | Department of Chemistry, Idaho State University, Campus Box 8023, Pocatello, ID 83209-8023, USA |
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Abstract: | 4,4′,5,5′-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4′,5,5′-tetraethynyldibenzo-24-crown-8 (10a,b) were prepared via a Sonogashira coupling reaction from tetraiodocrown ether 9. These highly conjugated crown ethers form complexes in CD2Cl2 with dibenzylammonium hexafluorophosphate in a 1:1 ratio. Emission spectrum of pseudorotaxane 11 shows a dramatic shift from the non-complexed precursor. |
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Keywords: | Crown ether Pseudorotaxane Self-assembly Alkyne Conjugation |
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