A cellulose-based chiral fluorescent sensor for aromatic nitro compounds with central, axial and planar chirality

作者：Ikai Tomoyuki^*; Suzuki Daisuke; Shinohara Ken ichi; Maeda Katsuhiro; Kanoh Shigeyoshi

来源：Polymer Chemistry, 2017, 8(14): 2257-2265.

DOI：10.1039/c7py00285h

Chiral sensing using fluorescent responses as output signals is an attractive technique for enantiodifferentiation in terms of its rapidity, high sensitivity, simplicity and high-throughput ability. However, because the reported sensors can only be applied to a limited type of chiral molecule (mainly compounds with a chiral center), it is still a great challenge to develop a powerful fluorescent sensor applicable to various types of chirality. Herein, we synthesized a novel chiral fluorescent sensor (Ce-3) containing a benzo [1,2-b: 4,5-b'] dithiophene-based p-conjugated group as a fluorescent signaling unit through a two-step polymer reaction, including carbamoylation and cross-coupling reactions, using microcrystalline cellulose as a starting material. The enantioselective fluorescence response of this modified cellulose to aromatic nitro compounds was investigated in solution and in the solid state. Ce-3 exhibited enantioselective fluorescence quenching for a wide range of aromatic nitro compounds with central, axial and planar chirality. Visual chiral detection based on a change of the visible emission color was also achieved with Ce-3 in conjunction with anthracene as an achiral fluorescent dye. A corresponding model molecule did not show any marked sensing ability, suggesting that the regular higher-order structure of Ce-3 plays a key role in this efficient chiral sensing.

• 出版日期2017-4-14