两个D-π-A型双氰基二苯乙烯双光子荧光染料的合成

The syntheses of Two Dicyanostilbene Two-Photon Fluorescence Dyes with a D-π-A Architecture

摘要:

该文合成了两个以双氰基二苯乙烯为母体的D-π-A型双光子荧光染料，并以其作为模型化合物就双氰基与末端取基对双光子吸收的影响进行了系统的研究。这两个化合物（DMO和DMA）具有大的双光子吸收截面（δ）。含有末端氨基的DMA较末端甲氧基的DMO具有更长的发射波长（λem(DMA) = 554 nm > λem(DMO) = 459 nm）、更大的双光子吸收截面（δ(DMA) = 3650 GM > δ(DMO) = 830 GM）和更高的荧光量子产率（η(DMA) = 0.456 >η(DMO) = 0.294）。理想的末端取代基不是烷氧基而是取代氨基。这类双氰基二苯乙烯染料拥有小的分子尺寸、大的δ（830–3650 GM）、长的发射波长（459−554 nm）和大的斯托克斯位移（St）（131−150 nm），是比较理想的用于双光子荧光标记和探针的发色团。

Abstract:

Two dicyanostilbene-derived two-photon fluorescence (TPF) dyes with a D-π-A architecture were synthesized as the model compounds to systematically study the effect of the dicyano and the terminal substituent on the two-photon absorption (TPA). These two compounds (DMO and DMA) exhibit very large two-photon absorption cross sections (δ). DMA with the terminal dimethylamino group has longer emission wavelength (λem(DMA) = 554 nm > λem(DMO) = 459 nm), larger δ (δ(DMA) = 3650 GM > δ(DMO) = 830 GM) and higher fluorescence quantum yield (η(DMA) = 0.456 > η(DMO) = 0.294) than with the terminal methoxy group. The ideal terminal substituent should not be the alkoxy group but the substitutedamino group. This class of dicyanostilbene dyes possess small molecule size, large δ (830–3650 GM), long-wavelength emission (459−554 nm) and large Stokes shift (131−150 nm), and are ideal chromophores for TPF labels and probes.