Novel Naphthalene Based Lariat-Type Crown Ethers Using Direct Single Electron Transfer Photochemical Strategy

Title
Novel Naphthalene Based Lariat-Type Crown Ethers Using Direct Single Electron Transfer Photochemical Strategy
Author(s)
조대원박혜정[박혜정]성남경[성남경]윤웅찬[윤웅찬]김수란[김수란]안소현[안소현]Patrick S. Mariano[Patrick S. Mariano]
Keywords
POLYDONOR-SUBSTITUTED PHTHALIMIDES; HEAVY-METAL IONS; PHOTOCYCLIZATION REACTIONS; CATION-BINDING
Issue Date
201312
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.34, no.12, pp.3681 - 3689
Abstract
This study explored a direct SET-photochemical strategy to construct a new family of thioene conjugated-naphthalamide fluorophore based lariat-crown ethers which show strong binding properties towards heavy metal ions. Irradiations of designed nitrogen branched (trimethylsilyl)methylthio-terminated polyethylenoxy-tethered naphthalimides in acidic methanol solutions have led to highly efficient photocyclization reactions to generate naphthalamide based lariat type thiadiazacrown ethers directly in chemo- and regio-selective manners which undergo very facile secondary dehydration reactions during separation processes to produce their corresponding amidoenethio ether cyclic products tethered with electron donating diethyleneoxy- and diethyenethio-side arm chains. Fluorescence and metal cation binding properties of the lariat type enamidothio products were examined. The photocyclized amidoenethio products, thioene conjugated naphthalamide fluorophore containing lariat-thiadiazacrowns exhibited strong fluorescence emissions in region of 330-450 nm along with intramolecular exciplex emissions in region of 450-560 nm with their maxima at 508 urn. Divalent cation Hg2+ and Pb2+ showed strong binding to sulfur atom(s) in side arm chain and atoms in enethiadiazacrown ether rings which led to significant enhancement of fluorescence from its chromophore singlet excited state and concomitant quenching of exciplex emission. The dual fluorescence emission responses towards divalent cations might provide a new guide for design and development of fluorescence sensors for detecting those metals.
URI
http://hdl.handle.net/YU.REPOSITORY/28105http://dx.doi.org/10.5012/bkcs.2013.34.12.3681
ISSN
0253-2964
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이과대학 > 화학생화학부 > Articles
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