Turn-on fluorogenic sensors based on an anthraquinone signaling unit for the detection of Zn(II) and Cd(II) ions

Chawanakorn Kongsak; Natthiti Chiangraeng; Puracheth Rithchumpon; Piyarat Nimmanpipug; Puttinan Meepowpan; Thawatchai Tuntulani; Praput Thavornyutikarn

doi:10.1039/d3ob01223a

Turn-on fluorogenic sensors based on an anthraquinone signaling unit for the detection of Zn(II) and Cd(II) ions

Org Biomol Chem. 2023 Sep 20;21(36):7367-7381. doi: 10.1039/d3ob01223a.

Authors

Chawanakorn Kongsak^{1

2}, Natthiti Chiangraeng¹, Puracheth Rithchumpon¹, Piyarat Nimmanpipug^{1

3}, Puttinan Meepowpan^{1

3}, Thawatchai Tuntulani⁴, Praput Thavornyutikarn^{1

3}

Affiliations

¹ Department of Chemistry, Faculty of Science, Chiang Mai University, 239 Huay Kaew Rd, Chiang Mai 50200, Thailand. praput.th@cmu.ac.th.
² Graduate School, Chiang Mai University, 239 Huay Kaew Rd, Chiang Mai 50200, Thailand.
³ Center of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand.
⁴ Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan Bangkok 10330, Thailand.

PMID: 37655509
DOI: 10.1039/d3ob01223a

Abstract

Turn-on fluorescent chemosensors based on an anthraquinone moiety, N,N'-(9,10-dioxo-9,10-dihydroanthracene-1,8-diyl)bis(2-(bis(pyridin-2-ylmethyl)amino)acetamide) (1) and N,N'-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(2-(bis(pyridin-2-ylmethyl)amino)acetamide) (2), have been successfully synthesized with the overall yields of 61% and 90%, respectively. The structures of both chemosensors 1 and 2 were elucidated using several spectroscopic techniques such as ¹H NMR, ¹³C NMR, 2D-NMR, FTIR and HRMS. The target chemosensor 1 is a promising tool for the detection of trace levels of d¹⁰ metal ions, such as Zn(II) and Cd(II) ions, by exhibiting a significant fluorescence enhancement via a turn-on photoinduced electron transfer (PET) mechanism with a rapid and highly reproducible signal, and low detection limit values of 0.408 μM and 0.246 μM, for Zn(II) and Cd(II), respectively.