Organic nanoparticles based on Lewis-pair formation: observation of prototropically controlled dual fluorescence†,Photochemical & Photobiological Sciences

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Organic nanoparticles based on Lewis-pair formation: observation of prototropically controlled dual fluorescence†
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2018-08-28 00:00:00 , DOI: 10.1039/c8pp00256h
Hiroshi Yao _{1,

2,

3,

4,

5} , Hikaru Minami _{5,

6,

7,

8} , Tomohito Funada _{5,

6,

7,

8}

Affiliation

We successfully synthesize fluorescent organic nanoparticles of a Lewis-pair consisting of an amino-type hydrogen-bonding molecule (Lewis base) and a borinate derivative (Lewis acid). 2-(2′-Aminophenyl)benzothiazole (o-ABT) is chosen as the fluorophore. This molecule has a transferable proton in the amino group, but it does not exhibit ESIPT (excited-state intramolecular proton transfer) reaction in solution and thus shows a single normal emission solely from the enamine form. Organic nanoparticles are prepared by the reprecipitation method in which the fluorophore (o-ABT) in conjunction with a Lewis acid (diphenylborinic anhydride; DPBA) dissolved in a good solvent is rapidly injected into water under sonication. Interestingly, the nanoparticles produced exhibit a characteristic dual fluorescence that can be ascribed to the enamine and imine tautomers of o-ABT generated in the ground-state prototropy, which can be revealed by UV-vis absorption and excitation spectroscopy, IR spectroscopy and computational approaches. In the o-ABT/DPBA Lewis-pair nanoparticles, highly Stokes-shifted emission from the imine tautomer is enhanced in comparison with that from the molecularly dissolved state, suggesting that the present nanofabrication methodology based on Lewis acid–base chemistry (or N–B bonding interaction) plays a key role in tuning the fluorescence colour for the new type of organic nanoparticle.

中文翻译：

基于路易斯对形成的有机纳米粒子：亲质性控制的双重荧光的观察†

我们成功地合成了由氨基型氢键分子（路易斯碱）和硼酸酯衍生物（路易斯酸）组成的路易斯对的荧光有机纳米粒子。选择2-（2'-氨基苯基）苯并噻唑（邻-ABT）作为荧光团。该分子在氨基中具有可转移的质子，但在溶液中不表现出ESIPT（激发态分子内质子转移）反应，因此仅显示出烯胺形式的单个正态发射。通过沉淀法制备有机纳米颗粒，其中荧光团（o-ABT）与溶于良好溶剂的路易斯酸（二苯基硼酸酐; DPBA）一起在超声处理下迅速注入水中。有趣的是，产生的纳米粒子表现出特征性的双重荧光，可以归因于基态质子体中生成的邻氨基苯甲酸的烯胺和亚胺互变异构体，这可以通过紫外可见吸收和激发光谱，红外光谱和计算方法来揭示。。在o-ABT / DPBA Lewis-pair纳米粒子，与分子溶解态相比，亚胺互变异构体的高斯托克斯位移发射得到增强，这表明当前基于Lewis酸碱化学（或N-B键相互作用）的纳米加工方法）在调节新型有机纳米粒子的荧光颜色方面起着关键作用。

更新日期：2018-08-28

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