121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-456
Subject Functionalized-8-hydroxybenzo[g]coumarin dyes: Synthesis, photophysical properties and two-photon imaging
Authors Sourav Sarkar, Kyo Han Ahn1,*
Chemistry, Pohang University of Science and Technology, Korea
1Department of Chemistry, Pohang University of Science and Technology, Korea
Abstract Umbelliferones have widely been used as a fluorogenic dye for developing molecular probes due to its easy synthesis, readily functionalizable arm and strong fluorescence property in the past decades. But because of their shorter absorption and emission wavelengths they suffer from severe limitations such as photobleaching, photodamage and autofluorescence during cellular imaging process. Moreover umbelliferones are not two-photon (TP) active which limits their use for tissue imaging.[1] Linearly benzene fused umbelliferones (benzo[g]coumarin) which are more conjugated posing a donor-acceptor type structure are expected to give promising results over typical umbelliferones but their efficient synthesis has always been a challenge. Herein we address a four-step synthetic route for the synthesis of 3-substituted-8-hydroxybenzo[g]coumarins, via simple Knovenagel condensation reaction which is effectively shorter and simpler than the previously reported ones.[2] Highlighted route here avoids use of harsh reaction conditions and follows a divergent approach effectively useful for screening dyes with most desirable properties. Synthesized dyes were photophysically characterized and subjected to both one-photon and two-photon imaging. Obtained results highlight their uniqueness because of enhanced optical properties including red shifted emission, TP absorption and large Stokes shifts, in addition to readily functionalizable arm for developing ratiometric-TP probes. Reference: [1] Tasior M, Kim D, Singha S, Krzeszewski M, Ahn KH, Gryko DT. J. Mater. Chem. C, 2015, 3, 1421 [2] Sarkar AR, Heo CH, Xu L, Lee HW, Si HY, Byun JW and Kim HM. Chem. Sci., 2016, 7, 766
E-mail sourav@postech.ac.kr