A Strongly Fluorescent Dye Featuring a Multiple N-doped Polycyclic Aromatic Hydrocarbon Skeleton

Abstract

This study presents the synthesis and characterization of a highly fluorescent compound derived from 5,11-dihydroquinoxalino[2,3-b]quinoxaline (tBQQ), which incorporates both sp³ and sp² nitrogen atoms into a polycyclic aromatic hydrocarbon skeleton. Starting from 3,6-di-tert-butyl-9H-carbazole, the target compound was obtained in moderate yield through a key condensation cyclization and subsequent oxidation reactions. The new compound exhibits excellent photophysical properties, including intense absorption and high photoluminescence quantum yield (96%). Taking together the electrochemical and computational studies, its bipolar nature is suggested. The fluorescence sensing capability toward acid was also revealed for tBQQ, attributable to the presence of sp² N atoms. This study provides an unexplored skeleton for the design of strongly fluorescent dyes toward various applications.

Keywords

Fluorescence - N-Heterocycles - π-Conjugated system - Polycyclic aromatic hydrocarbon - Organic semiconductor

Publication History

Received: 24 April 2025

Accepted after revision: 19 June 2025

Accepted Manuscript online:
20 June 2025

Article published online:
31 July 2025

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