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Updated: Jan 7, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Two Facile Isoindoline-1-One-Based Difluoroboron Compounds: Aggregation-Induced Emission, Mechanofluorochromism, and
Yuemei Li1, Yuhan Ren1, Bangcui Zhang1
1Yunnan Key Laboratory of Metal-Organic Molecular Materials and Device, School of Chemistry and Chemical Engineering, Kunming University, Kunming, China.
None:
To further investigate the optical properties of pyridyl-isoindoline-1-one derivatives and expand their practical applications, two novel difluoroboron dyes, a pyrenyl-substituted compound Isoin-py BF2 and an anthryl-substituted compound Isoin-en BF2, were conveniently synthesized in three steps. Both compounds exhibited aggregation-induced emission in DMSO/water mixtures and solid-state luminescence. Furthermore, their solutions could be used as developers for latent fingerprint imaging on three types of substrates. Interestingly, the imaging mechanism originates from a specific response of Isoin-py BF2 to oleic acid and of Isoin-en BF2 to lactic acid, both secreted in sweat. The developer based on Isoin-en BF2 could clearly reveal all three levels of fingerprint features, outperforming Isoin-py BF2 in detail resolution. Additionally, Isoin-py BF2 exhibited reversible mechanofluorochromic behavior due to a phase transition between crystalline states, enabling its application ink-free writing. In contrast, Isoin-en BF2 showed no mechanofluorochromism due to its strong crystallinity. This work provides a reference for the molecular design and development of boron-pyridyl-isoindoline-1-one-based dyes containing bulky π-conjugated substituents.
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