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首页> 外文期刊>Chemistry: A European journal >Solvatochromic Pyrene Analogues of Prodan Exhibiting Extremely High Fluorescence Quantum Yields in Apolar and Polar Solvents
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Solvatochromic Pyrene Analogues of Prodan Exhibiting Extremely High Fluorescence Quantum Yields in Apolar and Polar Solvents

机译：吡喃的溶剂变色P类似物在非极性和极性溶剂中具有极高的荧光量子产率

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Because organic fluorescent dyes can exhibit high sensitivity, rapid response, and good selectivity, they have attracted considerable attention for their potential application as fluorescent probes and as labels for monitoring chemical environments during biological events or conformational changes in multimolecular systems.~([1-3]) Organic fluorescent dyes can also be utilized as emitting materials for organic electronic devices.~([4, 5]) Therefore, a large number of organic fluorescent dyes have been developed, and criteria for designing them with the desired properties and functions have been established. For example, solvatochromism, which is a typical response of a dye to its environment, is indispensable in the use of dyes as imaging tools.~([2]) Solvatochromism is often achieved by introducing electronic donor and acceptor moieties, such as in "push-pulltype" dyes.~([6-17]) In addition, a high fluorescence quantum yield (QY) is important for the aforementioned applications and is generally achieved by extending the p-conjugation systems of appropriate chromophores,~([18]) for example, as observed in the relationship between pyrene (Φ_(Fl)=0.26 in chloroform)~([19]) and 1,3,6,8-tetraarylpyrene (Φ_(Fl)≈0.90 in dichloromethane).~([4]) However, to the best of our knowledge, dyes exhibiting both high QYs and strong solvatochromism in response to changes from apolar to polar media have not been developed. The development of dyes possessing these emission properties is difficult, and none that meets all of these criteria has been developed despite extensive research on versatile solvatochromic dyes.~([6-17, 20, 21]) Because of the aforementioned advantages of organic fluorescent dyes, especially as two-photon-excited fluorescence probes,~([7a, 21, 22]) criteria that take into account the necessary trade-offs should be established. To this end, we designed the pyrene derivatives PA [3,8-dibutyl-6-(piperidin-1-yl)pyrene-1-carbaldehyde] and PK [1-(3,8-dibutyl-6-(piperidin-1-yl)pyren-1- yl)butan-1-one]) (Scheme 1) based on Prodan (2-propionyl-6- dimethylaminonaphthalene), which is a well-known and widely used solvatochromic dye developed by Weber and Farris in 1979.~([6, 23]) We chose Prodan as the model compound because it fluoresces more strongly than other solvatochromic dyes in response to a wide range of polarity changes.~([6]) However, pyrene is superior as a building block to naphthalene in Prodan with respect to the absorption coefficient, QY,~([19]) and versatile modification options by substitution at the 1-, 3-, 6-, and 8-positions.~([5]) For example, we introduced a butyl group to the pyrene chromophore with the aim of improving its solubility and enhancing its QYs by increasing the oscillator strength.~([24]) Here, we report the synthesis and photophysical properties of PA and PK and demonstrate their outstanding photoluminescence properties, which include their extremely high QYs in both apolar (hexane) and polar (methanol) media as well as their strong solvatochromism.
机译：由于有机荧光染料显示出高灵敏度，快速响应和良好的选择性，因此它们作为荧光探针和在生物事件或多分子系统中构象变化期间监测化学环境的标记物的潜在应用吸引了相当多的关注。〜（[1- 3]）有机荧光染料也可以用作有机电子设备的发光材料。〜（[4，5]）因此，已经开发了许多有机荧光染料，并设计了具有所需特性和功能的标准。已经建立。例如，溶剂变色是一种染料对其周围环境的典型反应，在使用染料作为成像工具时必不可少。〜（[2]）溶剂变色通常是通过引入电子供体和受体部分来实现的，例如“推挽型”染料。〜（[6-17]）此外，高荧光量子产率（QY）对于上述应用很重要，通常通过扩展适当发色团的p共轭体系来实现（〜[18] ]），例如，从pyr（氯仿中的Φ_（Fl）= 0.26）〜（[19]）与1,3,6,8-四芳基py（二氯甲烷中的Φ_（Fl）≈0.90）之间的关系中观察到。 （[4]）然而，据我们所知，尚未开发出响应非极性介质向极性介质变化而显示出高QY和强溶剂化现象的染料。具有这些发射特性的染料的开发很困难，尽管对多功能溶剂变色染料进行了广泛的研究，但满足所有这些标准的染料都没有被开发出来。〜（[6-17，20，21]）由于上述有机荧光的优点染料，特别是作为双光子激发的荧光探针，应建立考虑到必要权衡的标准（[7a，21，22]）。为此，我们设计了derivatives衍生物PA [3,8-二丁基-6-（哌啶-1-基）py-1-甲醛]和PK [1-（3,8-二丁基-6-（哌啶-1 （Prote）（2-丙酰基-6-二甲基氨基萘）（方案1）是由Weber和Farris在2003年开发的一种广为人知的溶剂化变色染料1979.〜（[6，23]）之所以选择Prodan作为模型化合物，是因为它在响应各种极性变化时比其他溶剂变色染料发出更强的荧光。〜（[6]）然而，as作为建筑物的优越性在吸收系数QY，〜（[19]）和通用修饰选项上通过在1、3、6和8位上取代来封堵Prodan中的萘。例如（[5]） ，我们在the发色团中引入了一个丁基，目的是通过提高振动子强度来提高其溶解度并提高其QY。〜（[24]）在此，我们报道了PA和PK的合成和光物理性质，并证明了它们的邻位性出色的光致发光特性，包括在非极性（己烷）和极性（甲醇）介质中具有极高的QY，以及强大的溶剂致变色性。

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