3271-05-4Relevant articles and documents
Synthesis and Photooxygenation of 2,3,6-Trimethylfuronaphthopyrida-5,7-dione, A Potential Chemiluminescent Probe for Singlet Oxygen
Adam, Waldemar,Qian, Xuhong,Saha-Moeller, Chantu R.
, p. 417 - 422 (1993)
As potential chemiluminescent probe for singlet oxygen, the furonaphthalimide 4 was synthesized in five steps (ca. 25percent overall yield), by starting from commercially available 4-chloro-1,8-naphthalic anhydride; its photooxygenation at -10 deg C gave the cleavage product 6 of the intermediary dioxetane 5, which is thermally too labile for isolation and could not be detected even by low temperature NMR spectroscopy.The new 1,8-naphthalimide derivatives 3,4 and 6 were fully characterized and their absorption and fluorescence spectral properties were determined.
Naphthalimide/benzimide-based excited-state intramolecular proton transfer active luminogens: Aggregation-induced enhanced emission and potential for chemical modification
Wang, Rong,Ding, Ju,Zhang, Yanrong
, p. 9152 - 9161 (2019/06/17)
Fluorescent organic particles are important in a number of areas, including medical imaging; hence, the development of organic materials that exhibit aggregation-induced emissions is an important objective. To that end, we report the synthesis of naphthalimide- and benzimide-based 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives (HNIBT and HPIBT, respectively) that exhibit aggregation-induced emission enhancement (AIEE), in contrast to most naphthalimide- or benzimide-based derivatives that are prone to aggregation-induced quenching. Experimental studies like single-crystal X-ray diffraction analysis and theoretical calculations demonstrate that the ability to undergo excited-state intramolecular proton transfer is pivotal for AIEE. Further studies revealed that a terminal alkynyl chain at the N-imide site of HPIBT has little impact on the emission behavior of the resultant compound (HPIBT-yl). HPIBT-Pe, an amphiphilic molecule obtained through the click reaction of HPIBT-yl and a tetraethylene-glycol-derived azide, self-assembled to form highly photostable particles that have long-term fluorescence imaging potential in cellular environments.