Attachment of a 1,8-Naphthalimide Moiety to a Conjugated Polythiophene Efficiently Improves the Sensing Abilities of Naphthalimide-Based Materials
Attachment of a 1,8-Naphthalimide Moiety to a Conjugated Polythiophene Efficiently Improves the Sensing Abilities of Naphthalimide-Based Materials
复制标题
DOI：
10.1002/macp.201800436
复制
发表时间：
2019-02-01
影响因子：
2.5
通讯作者：
Zednik, Jiri
中科院分区：
文献类型：
--
作者：
Hladysh, Sviatoslav;Murmiliuk, Anastasiia;Zednik, Jiri
合成了一种新型的含1，8-萘酰亚胺的聚噻吩型共轭聚合物，其方法是对区域规则聚[3-(6-溴己基)噻吩基]进行两步修饰，包括溴端基与叠氮钠的亲核取代反应，然后与含有活性N-取代丙炔基团的新型1，8-萘酰亚胺衍生物进行铜催化的惠氏点击反应。用UV-Vis光谱、光致发光、核磁共振、光散射和等温滴定量热法对聚合物和高发光活性合成染料进行了广泛的研究。所制备的材料被认为是对不同过渡金属，如Fe2+、Co2+、Ni2+、Cu2+、Zn2+和Cd2+的潜在化学传感器。发光猝灭表明，这些材料对Fe2+的敏感度高于所测试的其他金属离子。此外，基于1，8-萘酰亚胺的共轭聚合物能够更有效地被Fe2+金属离子猝灭，与其母体1，8-萘酰亚胺衍生物相比，其浓度更低，结合常数更高，因此具有很高的传感器开发潜力。
A novel polythiophene-based conjugated polymer bearing 1,8-naphthalimide-based pendants is prepared by a two-step modification of regioregular poly[3-(6-bromohexyl)thiophene] involving a nucleophilic substitution reaction of the bromide end-groups with sodium azide followed by a robust, copper-catalyzed Huisgen click reaction with a novel 1,8-naphthalinmide derivative containing an active, N-substituted propyne group. Both the polymer and the highly luminescent-active synthesized dye are extensively studied in solution by UV-vis spectroscopy, photoluminescence, NMR, light-scattering and isothermal titration calorimetry. The materials prepared are considered potential chemosensors for different transition metals, such as Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Cd2+. Luminescence quenching shows that these materials have a higher sensitivity to Fe2+ than to the other metal ions tested. Moreover, the 1,8-naphthalimide-based conjugated polymer is more efficiently quenched by Fe2+ metal ions, at a significantly lower concentration and with a higher binding constant than its parent 1,8-naphthalimide derivative, thus indicating a high potential for sensor development.