ABSTRACT A new hyper-crosslinked 4-amino-1,8-naphthalimide Tröger’s base containing pyridinium covalent organic polymer, TBNap-COP, was synthesised and employed as a ‘turn-off’ fluorescent chemosensor for nitroaromatic explosives. TBNap-COP was synthesised in quantitative yield using a one-step nucleophilic substitution reaction between a dipyridyl scaffold (TBNap, bis-[N-(2-(pyridine-4-yl)ethyl)]-9,18-methano-1,8-naphthalimide-[b,f][1,5]diazocine) and 1,3,5-tris(bromomethyl)benzene by heating in DMF for 3 days. The formation and phase-purity of TBNap-COP were fully characterised by using various spectroscopic and microscopy analyses. The suspension of TBNap-COP in water showed strong fluorescence emission characteristics owing to the ‘push-pull’ based ICT transition and it was used as a fluorescent sensor for discriminative detection of nitroaromatic explosives. TBNap-COP displayed selective fluorescence quenching responses for phenolic-nitroaromatics, with particularly high sensitivity for picric acid which is a powerful secondary chemical explosive and a harmful environmental pollutant widely used in the dye industries.

中文翻译：

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含吡啶共价有机聚合物 (COP) 的超交联 4-氨基-1,8-萘二甲酰亚胺 Tröger 碱用于化学炸药的判别荧光传感

摘要 合成了一种新的超交联 4-氨基-1,8-萘二甲酰亚胺 Tröger 碱，含有吡啶共价有机聚合物 TBNap-COP，并用作硝基芳族炸药的“关闭”荧光化学传感器。使用双吡啶基支架（TBNap，双-[N-（2-（吡啶-4-基）乙基）]-9,18-methano-1之间的一步亲核取代反应以定量产率合成TBNap-COP，通过在 DMF 中加热 3 天，得到 8-萘二甲酰亚胺-[b,f][1,5] 重氮辛）和 1,3,5-三（溴甲基）苯。通过使用各种光谱和显微镜分析，TBNap-COP 的形成和相纯度得到了充分表征。由于基于“推拉”的 ICT 转变，TBNap-COP 在水中的悬浮液显示出强烈的荧光发射特性，并将其用作荧光传感器来区分检测硝基芳香族炸药。TBNap-COP 对苯酚-硝基芳烃显示出选择性荧光猝灭响应，对苦味酸具有特别高的灵敏度，苦味酸是一种强大的二次化学炸药，也是染料工业中广泛使用的有害环境污染物。