Green-synthesized single-benzene fluorophores exhibiting room-temperature phosphorescence and solid-state fluorescence for biological and optical applications

Schramm S, Müller C, Kramp M, Karothu DP, Zschommler JC, Commins P, Prestel T, Ibl V, Naumov P (2025)

Publication Type: Journal article

Publication year: 2025

Journal

Journal of Materials Chemistry C Royal Society of Chemistry

DOI: 10.1039/D5TC03134F

Abstract

Single-benzene fluorophores (SBFs) offer a minimalistic access to very small, bright, and electronically tunable emitters via push-pull effects. Herein, we report a green, solvent-free SNAr reaction of tetrafluoroterephthalonitrile (TFTPN) with five aliphatic amines that affords five SBFs in 70 -99% yields without chromatography. These dyes absorb at 400 -476 nm and emit in the range 520 -568 nm, achieving photoluminescence quantum yields of 51 - 68% in solution, up to 84% in polystyrene films, and up to 56% in crystalline form. X-ray crystallography and TD-DFT calculations confirmed their near-planar donor-acceptor geometries and large S₁-T₁ gaps, promoting efficient and fast fluorescence, alongside a polymer-induced exciplex delayed emissive component. Some SBFs crystallize as needle-like crystals that guide light with relatively low optical loss (~0.11 dB mm⁻¹) and can be formulated into tunable hybrid room-temperature-phosphorescent materials in inert matrices for timegated luminescence applications. Live-cell imaging using Arabidopsis thaliana roots demonstrates efficient tissue penetration and distinct staining patterns, highlighting their potential as minimal biolabels. This atom-economical multifunctional platform based on strongly emissive SBFs offers a sustainable blueprint for next-generation luminescent materials in photonic, security, and biological applications.

Authors with CRIS profile

Carolin Müller Juniorprofessur für die Theorie elektronisch angeregter Zustände

Involved external institutions

Hochschule für Bildende Künste Dresden DE Germany (DE) New York University Abu Dhabi (NYU Abu Dhabi) AE United Arab Emirates (AE) Hochschule für Technik und Wirtschaft Dresden (HTW Dresden) DE Germany (DE) Hochschule für Technik und Wirtschaft Berlin (HTW) DE Germany (DE)

How to cite

APA:

Schramm, S., Müller, C., Kramp, M., Karothu, D.P., Zschommler, J.C., Commins, P.,... Naumov, P. (2025). Green-synthesized single-benzene fluorophores exhibiting room-temperature phosphorescence and solid-state fluorescence for biological and optical applications. Journal of Materials Chemistry C. https://doi.org/10.1039/D5TC03134F

MLA:

Schramm, Stefan, et al. "Green-synthesized single-benzene fluorophores exhibiting room-temperature phosphorescence and solid-state fluorescence for biological and optical applications." Journal of Materials Chemistry C (2025).

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