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Synthesis and emissive properties of a series of tetrahydro (imidazo[1,5-a]pyrid-3-yl)phenols: a new class of large Stokes shift organic dyes
Dyes and Pigments ( IF 4.5 ) Pub Date : 2018-09-29 , DOI: 10.1016/j.dyepig.2018.09.069
Arianna Marchesi , Stefano Brenna , G. Attilio Ardizzoia

A series of 2-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-3-yl)phenols with different substituents (R) in the para position with respect to the hydroxyl group, was synthesized. The photophysical properties of these species have been investigated in dichloromethane solution: they displayed intense fluorescence when excited with UV light (310–340 nm), with λmax of emission varying in the range 430–530 nm and lifetime decay of few nanoseconds. A very large Stokes shift (up to 189 nm) and high absolute quantum yields (up to 0.72) were recorded for most of the compounds. Moreover, good tuning of the emission is observed according to the electronic features of the substituent R, and a linear correlation was found between the emission maxima of the compounds and the Hammett σp constants of R. Two of these (tetrahydroimidazo[1,5-a]pyridin-3-yl)phenols were then chosen for preliminary measurements of their photophysical properties when dispersed in a host polymeric matrix (PMMA).



中文翻译:

一系列四氢(咪唑并[1,5 - a ]吡啶-3-基)苯酚的合成和发射性质:一类新型的大斯托克斯位移有机染料

合成了一系列2-(5,6,7,8-四氢咪唑并[1,5- a ]吡啶-3-基)相对于羟基的位具有不同取代基(R)的酚。已经在二氯甲烷溶液中研究了这些物种的光物理特性:当它们被紫外光(310–340 nm)激发时,它们表现出强烈的荧光,最大λ发射波长在430-530 nm范围内变化,寿命衰减几纳秒。对于大多数化合物,记录到非常大的斯托克斯位移(最大189 nm)和很高的绝对量子产率(最大0.72)。此外,发射的良好调谐根据取代基R的电子特征观察到,并且发现的化合物的发射最大值和哈米特σ之间的线性相关p这些(四氢的R.两个常数[1,5 -然后选择一种]吡啶基-3-基)苯酚,以初步测定它们分散在主体聚合物基质(PMMA)中时的光物理性质。

更新日期:2018-09-29
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