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A General Synthetic Approach and Photophysical Properties of Regioselectively Fluorinated [5]- and [6]-Helical Bispiroindenofluorenes.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-08-05 , DOI: 10.1002/cplu.202000434
Ilaria Caivano 1 , Zdeněk Tošner 2 , Ivana Císařová 3 , David Nečas 1 , Martin Kotora 1
Affiliation  

A first series of fluorinated [n]helical compounds (n=5 and 6) with the dihydroindenofluorene scaffold was prepared in 5 or 9 (octafluorinated dihydroindenofluorene) steps and their photophysical properties were determined. Rh‐catalyzed intramolecular [2+2+2] cyclotrimerization of triyndiols, which were prepared in a modular fashion from simple starting material such as fluorinated haloarylcarbaldehydes, to the intermediate [n]helical dihydroindeno[2,1‐c]fluorene‐5,8‐diols was the crucial synthetic step and proceeded with high efficacy. Their further transformation gave the desired selectively fluorinated bispirodihydroindeno[2,1‐c]fluorenes. Their absorption and emission spectra were recorded. The fluorescence quantum yields were up to 92 % and the emission maxima were red‐shifted in comparison with their non‐fluorinated counterparts (386‐413 nm).

中文翻译:

区域选择性氟化的[5]-和[6]-螺旋双螺并茚并芴的一般合成方法和光物理性质。

在5或9(八氟化二氢茚芴)步骤中制备了带有二氢茚并芴支架的第一批氟化[n]螺旋化合物(n = 5和6),并确定了它们的光物理性质。铑催化的分子内[2 + 2 + 2] triyndiols,起始材料如氟化haloarylcarbaldehydes其被以模块化的方式来制备,从简单的环三聚,到中间[n]的螺旋二氢茚并[2,1- c ^ ]芴-5, 8-二醇是关键的合成步骤,并具有很高的功效。他们的进一步转化得到所需的选择性氟化双螺二氢茚并[2,1- c芴。记录它们的吸收和发射光谱。与未氟化的对应物(386-413 nm)相比,荧光量子产率高达92%,发射最大值发生了红移。
更新日期:2020-09-03
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