@article{vonlanthen_connelly_deiters_linden_finney_2014, title={Thiourea-Based Fluorescent Chemosensors for Aqueous Metal Ion Detection and Cellular Imaging}, volume={79}, ISSN={["1520-6904"]}, DOI={10.1021/jo500710g}, abstractNote={We describe three significant advances in the use of thioureas as reporting elements for metal-responsive fluorescent chemosensors. First, on the basis of the crystal structure of a chemosensor analogue, we provide a deeper understanding of the details of the thiourea coordination environment. Second, we describe a new generation of chemosensors with higher affinities for Zn(2+) and Cd(2+) than were observed for earlier probes, expanding the scope of this type of probe beyond Hg(2+) detection. Third, we show that a thiourea-based chemosensor can be employed for fluorescence microscopy imaging of Hg(2+) ion concentrations in living mammalian cells.}, number={13}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Vonlanthen, Mireille and Connelly, Colleen M. and Deiters, Alexander and Linden, Anthony and Finney, Nathaniel S.}, year={2014}, month={Jul}, pages={6054–6060} } @article{kathayat_finney_2013, title={Sulfoxides as Response Elements for Fluorescent Chemosensors}, volume={135}, ISSN={["0002-7863"]}, DOI={10.1021/ja407099a}, abstractNote={Sulfoxides are shown to be viable reporting groups for fluorescent chemosensor development. Metal coordination of sulfoxide-appended fluorophores suppresses excited-state pyramidal inversion of the sulfoxide, leading to enhanced fluorescence emission. This new structural motif allows the construction of fluorescent chemosensors that do not require nitrogen coordination as part of the signaling process, that have a range of selectivities and affinities for oxophilic metal ions, and that can function in water.}, number={34}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Kathayat, Rahul S. and Finney, Nathaniel S.}, year={2013}, month={Aug}, pages={12612–12614} } @article{rocha_finney_2013, title={Systematic Evaluation of 2,6-Linked Pyridine-Thiophene Oligomers}, volume={78}, ISSN={["1520-6904"]}, DOI={10.1021/jo401735g}, abstractNote={An efficient synthesis of alternating 2,6-linked pyridine-thiophene (Py-Th) oligomers allows systematic evaluation of their optical and electrochemical properties. The six- and eight-ring oligomers are revealed to be brightly luminescent, even in the solid state. The oligomers are easily reduced but cannot be electrochemically oxidized. The longer oligomers have reduction potentials similar to those reported for pyridine-thiophene polymers of less defined structure. Protonation of the pyridine or substitution at C4 are shown to further modulate the electronic properties and, in combination with the low-lying absolute LUMO energies, these data suggest that the compounds are potential n-type materials worthy of further study.}, number={22}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Rocha, Silvia V. and Finney, Nathaniel S.}, year={2013}, month={Nov}, pages={11255–11261} } @article{vonlanthen_finney_2013, title={Thioureas as Reporting Elements for Metal-Responsive Fluorescent Chemosensors}, volume={78}, ISSN={["1520-6904"]}, DOI={10.1021/jo4003129}, abstractNote={Proof that sulfur is a viable reporting element for the development of fluorescent chemosensors for metal ions is presented. To date, the majority of metal-responsive fluorescent chemosensors have relied on metal-nitrogen coordination to provide a fluorescence response, most commonly by suppressing photoinduced electron transfer (PET) quenching. While chemosensors with direct application to biology, medicine, and analytical chemistry have been so developed, reliance on the coordination chemistry of nitrogen remains a practical and conceptual limitation. Building on the fact that thioureas can quench fluorescence emission by PET, it is shown that the quenched emission of thiourea-appended naphthalimides can be restored by metal binding and that metal affinity and selectivity can be controlled through structural modification of the thiourea substituents. Further, such chemosensors can function in aqueous media and, unlike nitrogen-based chemosensors, are unresponsive to increases in [H(+)]. Given that the coordination properties of sulfur are distinct from those of nitrogen, this work lays the foundation for the development of a new class of interesting and useful metal-responsive fluorescent probes.}, number={8}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Vonlanthen, Mireille and Finney, Nathaniel S.}, year={2013}, month={Apr}, pages={3980–3988} }