Tellurium analogues of rosamine and rhodamine dyes:: Synthesis, structure, 125Te NMR, and heteroatom contributions to excitation energies
Tellurium analogues of rosamine and rhodamine dyes:: Synthesis, structure, 125Te NMR, and heteroatom contributions to excitation energies
复制标题
DOI：
10.1021/om700846m
复制
发表时间：
2007-12-03
期刊：
影响因子：
2.8
通讯作者：
Detty, Michael R.
中科院分区：
文献类型：
--
作者：
Calitree, Brandon;Donnelly, David J.;Detty, Michael R.
通过将格氏试剂或有机锂试剂添加到硫代黄原酮前驱体中，制备了第一批含碲的罗萨明和罗丹明染料类似物。报道了这两种染料及其前体的Te-125谱。对其中一种衍生物进行了X-射线晶体结构表征，发现其具有一个接近平面的碲氧钛核，其中一个9-芳基取代基与该核几乎垂直。用密度泛函理论(DFT)和含时密度泛函(TDDFT)计算分析了实验观察到的激发波长的变化趋势。计算表明，杂原子孤对轨道的参与是造成这一趋势的原因。
The first tellurium-containing analogues of the rosamine and rhodamine dyes were prepared by the addition of Grignard or organolithium reagents to telluroxanthone precursors. The Te-125 spectra of both the dyes and the telluroxanthone precursors are reported. One derivative was characterized by X-ray crystallography and was found to have a nearly planar telluroxanthylium core with a 9-aryl substituent held nearly orthogonal to the core. Density functional theory (DFT) and time-dependent DFT (TDDFT) calculations were performed to analyze the trends for the excitation wavelengths observed experimentally. The computations indicated that participation of the heteroatom lone pair orbitals is responsible for this trend.