A General Synthetic Approach and Photophysical Properties of Regioselectively Fluorinated [5]- and [6]-Helical Bispiroindenofluorenes.,ChemPlusChem

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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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