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Controlling the fluorescence quantum yields of benzothiazole-difluoroborates by optimal substitution

Patryk Rybczyński, Manon H. E. Bousquet, Anna Kaczmarek‐Kędziera, Beata Jędrzejewska, Denis Jacquemin, Borys Ośmiałowski

2022Chemical Science43 citationsDOIOpen Access PDF

Abstract

the limiting molecular vibrations by aggregation. However, the subtle balance between the abundant possible radiative and non-radiative decay pathways makes the final picture exceptionally sophisticated. In the present study, a series of nine fluorophores obtained by peripheral substitution with two relatively mild electron donating and electron withdrawing groups are reported. The obtained fluorescence quantum yields range from dark to ultra-bright and the extreme values are obtained for the isomeric molecules. These severe changes in emission efficiency have been shown to arise from the complex relationship between the Franck-Condon excited state and conical intersection position. The experimental findings are rationalized by the advanced quantum chemical calculations delivering good correlation between the measured emission parameters and theoretical radiative and internal conversion rate constants. Therefore, the described substituent exchange provides a method to rigorously adjust the properties of molecular probes structurally similar to thioflavin T.

Topics & Concepts

BenzothiazoleSubstitution (logic)FluorescenceQuantumChemistryCombinatorial chemistryComputer sciencePhysicsOrganic chemistryQuantum mechanicsProgramming languageLuminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionOrganic Light-Emitting Diodes Research
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