Counterion Pairing Effects on a Flavylium Heptamethine Dye.
Counterion Pairing Effects on a Flavylium Heptamethine Dye.
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DOI：
10.1111/php.13531
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发表时间：
2022-03
影响因子：
3.3
通讯作者：
Sletten EM
中科院分区：
文献类型：
--
作者：
Pengshung M;Cosco ED;Zhang Z;Sletten EM
多甲川荧光团由于其有利的物理化学性质，促进了生物和材料科学的进步。然而，保持单体状态的需要会严重限制染料的实用性和可加工性。高浓度的荧光团可导致聚集并否定单体的有益的生物物理性质。另一个问题是"跨越花青极限"，其中聚甲炔支架内的离域被破坏，产生不对称状态的存在，从而降低其物理行为。在这里，我们试图克服这些限制，探索阳离子黄铵七甲川支架上的阴离子交换。通过增加阴离子的大小和疏水性，我们可以有效地调节聚甲川染料内的离子配对程度。有趣的是，我们发现，与更常用的吲哚菁菁染料相比，离子配对对生物物理性质的影响对于黄环七甲川支架是微妙的。利用更大的弱配位阴离子使flavylium七甲川荧光团在非极性溶剂中的溶解度成为可能，否则这无法实现。即使具有比经典花菁染料更微妙的效果，黄酸聚甲川染料上的阴离子交换也具有进一步操纵这些低能染料的性质的潜力。
Polymethine fluorophores have facilitated the advance of biological and material sciences, due to their advantageous photophysical properties. However, the need to maintain a monomeric state can severely limit the utility and processability of dyes. High concentrations of fluorophore can lead to aggregation and negate the beneficial photophysical properties of monomers. Another concern is “crossing the cyanine limit” in which delocalization within the polymethine scaffold is broken, producing the presence of an asymmetric state diminishing its photophysical behavior. Herein, we attempt to overcome these limitations by exploring anion exchange on a cationic flavylium heptamethine scaffold. By increasing the size and hydrophobicity of the anion, we can effectively tune the degree of ion pairing within the polymethine dye. Interestingly, we found that the effect of ion pairing on photophysical properties was subtle for the flavylium heptamethine scaffold in comparison to the more commonly used indolenine cyanine dye. Utilizing larger weakly coordinating anions enabled solubility of the flavylium heptamethine fluorophore in nonpolar solvents, which could otherwise not be achieved. Even with more subtle effects than classic cyanine dyes, anion exchange on flavylium polymethine dyes holds potential for further manipulation of the properties of these low energy dyes.
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DOI：
10.3390/molecules26030524
发表时间：
2021-01-20
期刊：
Molecules (Basel, Switzerland)
影响因子：
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