title: A practical approach for the preparation of monofunctional azulenyl squaraine dye.
abstract: The synthesis of monofunctional azulenyl squaraine dye NIRQ(700) is described. The essential azulene intermediate 3, 1-(methoxycarbonyl)-2-methylazulene, was achieved via [8+2] cycloaddition between lactone 2, 2H-3-methoxycarbonyl-cyclohepta[b]furan-2-one, and the in situ generated vinyl ethers under high temperature and pressure conditions. Methylation on the cycloheptatriene ring of 2-methyl azulene 6 via Meisenheimer-type intermediate following Schrott's method formed the carboxylic acid intermediate 9, 3-(2-methyl-azulen-4-yl)-propionic acid. Condensation of 9 with squaric acid provided the title compound NIRQ(700) at moderate yields. The non-fluorescent squaraine dye NIRQ(700) absorbed in a 600-700 nm range and potentially can be used to quench a number of available NIR fluorochromes in order to extend the spectrum of biological quenching assays.
authors.affiliation: Center for Molecular Imaging Research, Massachusetts General Hospital, Harvard Medical School, Charlestown, MA 02129, USA.
authors.forename: Wellington
authors.initials: W
authors.lastname: Pham
authors.forename: Ralph
authors.initials: R
authors.lastname: Weissleder
authors.forename: Ching-Hsuan
authors.initials: CH
authors.lastname: Tung