Hong Janice W, Gaylord Brent S, Bazan Guillermo C
Department of Chemistry, University of California, Santa Barbara, CA 93106, USA.
J Am Chem Soc. 2002 Oct 9;124(40):11868-9. doi: 10.1021/ja027170r.
Water soluble paracyclophane chromophore dimers provide optical reporters that show little sensitivity to surfactants and thus are ideal for biosensor design. Strong intramolecular delocalization circumvents complications from intermolecular delocalization in spontaneously formed aggregates. The synthesis of 2 involves a novel TBAT deprotection/butane sultone ring-opening sequence, which should be general for the preparation of water-soluble conjugated oligomers and polymers.
水溶性对环芳烷发色团二聚体提供了对表面活性剂几乎不敏感的光学报告分子，因此是生物传感器设计的理想选择。强烈的分子内离域避免了自发形成聚集体时分子间离域带来的复杂性。化合物2的合成涉及一种新颖的四丁基铵三氟乙酸盐脱保护/丁烷磺酸内酯开环序列，这对于制备水溶性共轭低聚物和聚合物应该具有通用性。
