Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-11 , DOI: 10.1016/j.tet.2018.05.019 Ryo Hirata , Ayame Torii , Kenichi Kawano , Shiroh Futaki , Ayumi Imayoshi , Kazunori Tsubaki
Fluorescent dyes possessing a variety of arylacetylenes at the 9-position of a xanthene skeleton were synthesized and their optical properties were investigated. The π system effectively expanded over the xanthene skeleton and the aryl group through the triple bond. Starting from the emission wavelength (λem) of 9-methyl xanthene 20 in basic DMSO solution at 536 nm, the emission wavelengths gradually shifted to the red region for methylacetylene 17 (λem = 600 nm), phenylacetylene 5 (λem = 636 nm), and p-CF3-phenylacetylene 11 (λem = 660 nm). On the basis of these data, we estimated the substituent effects for the red shift on the emission wavelength and rationally explained the results by DFT calculations. Furthermore, potential applicability of these fluorescent dyes to cell staining was exemplified.
中文翻译:
含芳基乙炔的x吨染料的开发:乙炔连接基和芳基上的取代基的作用
合成了在a吨骨架9位具有多种芳基乙炔的荧光染料,并对其光学性质进行了研究。π系统通过三键有效地扩展了the吨骨架和芳基。从碱性DMSO溶液中9-甲基x吨20的发射波长(λem)在536 nm开始,发射波长逐渐移至甲基乙炔17(λem = 600 nm),苯基乙炔5(λem = 636 )的红色区域nm)和p -CF 3-苯基乙炔11(λem = 660 nm)。根据这些数据,我们估计了红移对发射波长的取代作用,并通过DFT计算合理地解释了结果。此外,举例说明了这些荧光染料对细胞染色的潜在适用性。