Inorganic Chemistry, volume 46, issue 25, pages 10564-10577
Cu2+ colorimetric sensing and fluorescence enhancement and Hg2+ fluorescence diminution in "scorpionate"-like tetrathienyl-substituted boron-dipyrrins.
1
Department of Chemistry and School of Molecular Science (BK 21), KAIST, Daejeon 305-701, Korea, and Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027
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Publication type: Journal Article
Publication date: 2007-11-09
Journal:
Inorganic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.6
ISSN: 00201669, 1520510X
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Four novel tetrathienyl-substituted boron-dipyrrin-type (BODIPY-type) complexes, 3-(R')-4,4-di(R')-8-R-4-bora-3a,4a-diaza-s-indacene (4a, R = 2-T, R' = 2-T; 4b, R = 3-T, R' = 2-T; 5a, R = 2-T, R' = 3-T; 5b, R = 3-T, R' = 3-T; T = thienyl) have been prepared and fully characterized to explore patterns of stoichiometric Mn+ recognition in solution. Treatment of the respective parent BF2 dipyrrin with 2- or 3-thienyllithium gave the unexpected asymmetric tetrathienyl-substituted products in 8.5-35% yield. Compounds 4a and 4b bear a neutral "scorpionate"-like [SSS] tridentate binding pocket. Extensive NMR and UV-vis spectroscopic studies were performed on 4a-5b; 5a, 4b, and 5b were structurally characterized. The PhiF values for 4a-5b all decrease compared to the BF2-containing parent molecules (0.00058, 0.012, 0.00090, and 0.0051, respectively), with lambda(abs,max) values (epsilon, M(-1) cm(-1)) of 563 (44,000), 553 (29,000), 539 (33,000), and 531 (44,000) nm, respectively, and Stokes' shifts of 25-36 nm. Upon treatment with metal ion (Ca2+, Cs+, Mn2+, Co2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, Pb2+) perchlorate salts, the solution of 4b undergoes rapid pink-to-clear switch-off behavior upon Cu2+ addition (10 microM scale) with smaller effects seen for 4a. Further, there were 2- to 19-fold Cu2+ fluorescence enhancements for these ligands. Cu2+- and Hg2+-L (L = 4a-5b) binding was modeled, and response patterns for Mn+-L 1:1 molar solutions upon Cu2+ addition were measured. Upon treatment with Hg2+, all ligand solutions show a significant fluorescence decrease accompanied by minor absorption increases. The UV-vis spectroscopic detection limit for Cu2+ and Hg2+ is approximately 270 ppb and approximately 1.7 ppm, respectively; the naked eye detection limit for Cu2+ with 4b (1.0 x 10(-5) M) is approximately 23 microM. DFT calculations gave HOMO-LUMO gaps of 478 (4a), 462 (4b), 448 (5a), and 442 nm (5b). Molecular orbital diagrams for 4a-5b revealed that the HOMO and LUMO electron density is distributed onto the 3-position-thienyl group and to a lesser degree the B(thienyl)2 moiety.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
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Choi S. et al. Cu2+ colorimetric sensing and fluorescence enhancement and Hg2+ fluorescence diminution in "scorpionate"-like tetrathienyl-substituted boron-dipyrrins. // Inorganic Chemistry. 2007. Vol. 46. No. 25. pp. 10564-10577.
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Choi S., Pang K., Kim K., Churchill D. G. Cu2+ colorimetric sensing and fluorescence enhancement and Hg2+ fluorescence diminution in "scorpionate"-like tetrathienyl-substituted boron-dipyrrins. // Inorganic Chemistry. 2007. Vol. 46. No. 25. pp. 10564-10577.
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TY - JOUR
DO - 10.1021/ic701101j
UR - https://doi.org/10.1021%2Fic701101j
TI - Cu2+ colorimetric sensing and fluorescence enhancement and Hg2+ fluorescence diminution in "scorpionate"-like tetrathienyl-substituted boron-dipyrrins.
T2 - Inorganic Chemistry
AU - Choi, Shin-Hei
AU - Pang, Keliang
AU - Kim, Kibong
AU - Churchill, David G.
PY - 2007
DA - 2007/11/09 00:00:00
PB - American Chemical Society (ACS)
SP - 10564-10577
IS - 25
VL - 46
SN - 0020-1669
SN - 1520-510X
ER -
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@article{2007_Choi,
author = {Shin-Hei Choi and Keliang Pang and Kibong Kim and David G. Churchill},
title = {Cu2+ colorimetric sensing and fluorescence enhancement and Hg2+ fluorescence diminution in "scorpionate"-like tetrathienyl-substituted boron-dipyrrins.},
journal = {Inorganic Chemistry},
year = {2007},
volume = {46},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021%2Fic701101j},
number = {25},
pages = {10564--10577},
doi = {10.1021/ic701101j}
}
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Choi, Shin-Hei, et al. “Cu2+ colorimetric sensing and fluorescence enhancement and Hg2+ fluorescence diminution in "scorpionate"-like tetrathienyl-substituted boron-dipyrrins..” Inorganic Chemistry, vol. 46, no. 25, Nov. 2007, pp. 10564-10577. https://doi.org/10.1021%2Fic701101j.