TY  - JOUR
A1  - Soyka, J. P.
A1  - Witte, J. F.
A1  - Wiesner, A.
A1  - Krappe, A. R.
A1  - Wehner, D.
A1  - Alnicola, N.
A1  - Paulus, B.
A1  - Resch-Genger, Ute
A1  - Eigler, S.
T1  - [3]Radialene Fluorophores with pH-Switchable Emission and Stable Absorption Maxima
JF  - European journal of organic chemistry
N2  - The first push–pull quino [3]radialene fluorescent dye is reported. Herein, the novel bis(dicyanomethylene)-[3]radialene electron acceptor is connected to a benzimidazole donor. With protonation, a substantial redshift of fluorescence wavelength is observed, while the absorption maximum remains stable. This process is accompanied with an increased fluorescence quantum yield to about 70%. Further, the findings are explained by a combined experimental and theoretical approach, and it is found that vibronic coupling plays a crucial role. This study highlights the yet unexplored potential of [3]radialene-based motifs for the design of environment-responsive fluorophores.
KW  - DADQ
KW  - Nanographene
KW  - fluorescence
KW  - Nano
KW  - Particle
KW  - Synthesis
KW  - Characterization
KW  - Advanced material
KW  - Quantum yield
KW  - Photophysic
KW  - pH
KW  - Probe
KW  - Sensor
KW  - Lifetime
KW  - Polarity
PY  - 2025
UR  - https://nbn-resolving.org/urn:nbn:de:kobv:b43-642147
DO  - https://doi.org/10.1002/ejoc.202500669
SN  - 1099-0690
SP  - 1
EP  - 6
PB  - Wiley-VCH
CY  - Weinheim
AN  - OPUS4-64214
LA  - eng
AD  - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany
ER  -