Cyanostyryl‐Guanidiniocarbonyl‐Pyrrole Amphiphiles: From Aggregation‐Induced Emission to Photodimerization, Self‐Assembly, and Bioimaging

Two Cyanostyryl-guanidiniocarbonyl-pyrrole based amphiphiles are synthesized and examined in detail. In addition to achieving aggregation-induced emission from self-assembly, resulting in nanoparticles, it was found that the observed [2 + 2] photocycloaddition tunes the photophysical properties. The guanidiniocarbonyl-pyrrole component of these hybrid luminophores is shown to bind oxo-anions, such as pyrene-tetracarboxylate, as confirmed by fluorescence lifetime measurements. Moreover, both amphiphiles are used in bio-imaging experiments with HeLa cells, demonstrating effective cellular uptake.

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Publication Details

Journal
ChemPlusChem
Published
2025-09-23
DOI
https://doi.org/10.1002/cplu.202500542
Primary Topic
Luminescence and Fluorescent Materials
Type
article
Field-Weighted Citation Impact
0.00

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article

Cyanostyryl‐Guanidiniocarbonyl‐Pyrrole Amphiphiles: From Aggregation‐Induced Emission to Photodimerization, Self‐Assembly, and Bioimaging

Nina Schulze, Jens Voskuhl, Thulaseedharan Nair Sailaja Sidharth, Shirley K. Knauer et al.
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Luminescence and Fluorescent Materials
article

Cyanostyryl‐Guanidiniocarbonyl‐Pyrrole Amphiphiles: From Aggregation‐Induced Emission to Photodimerization, Self‐Assembly, and Bioimaging

Nina Schulze, Jens Voskuhl, Thulaseedharan Nair Sailaja Sidharth, Shirley K. Knauer, Florian Uteschil, Kevin Rudolph, Elisabeth Verheggen, Alexander Höing, Felix C. Niemeyer, Johannes Koch, L. Hofmann
article en

Abstract

Two Cyanostyryl-guanidiniocarbonyl-pyrrole based amphiphiles are synthesized and examined in detail. In addition to achieving aggregation-induced emission from self-assembly, resulting in nanoparticles, it was found that the observed [2 + 2] photocycloaddition tunes the photophysical properties. The guanidiniocarbonyl-pyrrole component of these hybrid luminophores is shown to bind oxo-anions, such as pyrene-tetracarboxylate, as confirmed by fluorescence lifetime measurements. Moreover, both amphiphiles are used in bio-imaging experiments with HeLa cells, demonstrating effective cellular uptake.

ChemPlusChemVol. 90(12)
University of Duisburg-Essen (DE)
Deutsche Forschungsgemeinschaft, Interdisciplinary Center for Analytics on the Nanoscale, University of Duisburg-Essen
Openalex Percentile: Top 80%
Luminescence and Fluorescent Materials
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Cyanostyryl‐Guanidiniocarbonyl‐Pyrrole Amphiphiles: From Aggregation‐Induced Emission to Photodimerization, Self‐Assembly, and Bioimaging — Nina Schulze, Jens Voskuhl, et al. · ChemPlusChem (2025) | TGRS Research Map | TGRS