The fluorescence of a chelating two-photon-absorbing dye is enhanced with the addition of transition metal ions but quenched in the presence of acid

David J. Stewart; Stephanie L. Long; Zhenning Yu; Ramamurthi Kannan; Alexandr Mikhailov; Aleksander Rebane; Loon-Seng Tan; Joy E. Haley

doi:10.1117/12.2236658

23 September 2016 The fluorescence of a chelating two-photon-absorbing dye is enhanced with the addition of transition metal ions but quenched in the presence of acid

David J. Stewart, Stephanie L. Long, Zhenning Yu, Ramamurthi Kannan, Alexandr Mikhailov, Aleksander Rebane, Loon-Seng Tan, Joy E. Haley

Author Affiliations +

Proceedings Volume 9939, Light Manipulating Organic Materials and Devices III; 993904 (2016) https://doi.org/10.1117/12.2236658
Event: SPIE Organic Photonics + Electronics, 2016, San Diego, California, United States

Abstract

A pseudo-symmetric two-photon absorbing dye (1) containing a central piperazine unit substituted with (benzothiazol-2- yl)-9,9-diethylfluoren-2-yl pendant groups has been synthesized and characterized. The molecule has a two-photonabsorption cross-section of σ₂ = 140 GM in tetrahydrofuran at ~ 740 nm and shows significant solvatochromism in the excited-state fluorescence spectra. The emission spectra broaden and the maxima bathochromically shift from 411 nm to 524 nm in n-hexane and acetonitrile, respectively. Moreover, the central piperazine moiety serves as a potential chelation site for ions. Addition of copper(I) hexafluorophosphate and zinc(II) triflate in acetonitrile indicate ground-state complexation with a shift in the emission maximum from 524 nm to 489 nm and 487 nm, respectively. Interestingly, the newly formed Cu and Zn complexes are more strongly emissive than the free dye. Finally, addition of p-toluenesulfonic acid in tetrahydrofuran also blue-shifts the emission maximum, but the intensity is quenched. Due to the photophysical changes induced by addition of metal ions and protons, the dye shows promise as a potential sensor.

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David J. Stewart, Stephanie L. Long, Zhenning Yu, Ramamurthi Kannan, Alexandr Mikhailov, Aleksander Rebane, Loon-Seng Tan, and Joy E. Haley "The fluorescence of a chelating two-photon-absorbing dye is enhanced with the addition of transition metal ions but quenched in the presence of acid", Proc. SPIE 9939, Light Manipulating Organic Materials and Devices III, 993904 (23 September 2016); https://doi.org/10.1117/12.2236658

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