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


Vol. 34,  No. 12, pp. 3681-3689, Dec.  2013
10.5012/bkcs.2013.34.12.3681


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  Abstract

This study explored a direct SET-photochemical strategy to construct a new family of thioene conjugatednaphthalamide fluorophore based lariat-crown ethers which show strong binding properties towards heavy metal ions. Irradiations of designed nitrogen branched (trimethylsilyl)methylthio-terminated polyethylenoxytethered 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 nm. 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.

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  Cite this article

[IEEE Style]

H. J. Park, N. K. Sung, S. R. Kim, S. H. Ahn, U. C. Yoon, D. W. Cho, P. S. Mariano, "Novel Naphthalene Based Lariat-Type Crown Ethers Using Direct Single Electron Transfer Photochemical Strategy," Bulletin of the Korean Chemical Society, vol. 34, no. 12, pp. 3681-3689, 2013. DOI: 10.5012/bkcs.2013.34.12.3681.

[ACM Style]

Hea Jung Park, Nam Kyung Sung, Su Rhan Kim, So Hyun Ahn, Ung Chan Yoon, Dae Won Cho, and Patrick S. Mariano. 2013. Novel Naphthalene Based Lariat-Type Crown Ethers Using Direct Single Electron Transfer Photochemical Strategy. Bulletin of the Korean Chemical Society, 34, 12, (2013), 3681-3689. DOI: 10.5012/bkcs.2013.34.12.3681.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949