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Isoquinoline-Based TQEN Family as TPEN-Derived Fluorescent Zinc Sensors
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KYOUSEI Science Center.
, ‡Division of Functional Material Science.
Section:Abstract
The hexadentate nitrogen ligands 1-isoTQEN (N,N,N’,N’-tetrakis(1-isoquinolylmethyl)ethylenediamine) and 3-isoTQEN (N,N,N’,N’-tetrakis(3-isoquinolylmethyl)ethylenediamine) have been prepared. The structures of these ligands are based on that of TPEN (N,N,N’,N’-tetrakis(2-pyridylmethyl)ethylenediamine). The introduction of a benzene ring into TPEN affords fluorescence ability upon zinc-ion binding. Compared to the quinoline isomer TQEN, isoquinoline derivatives 1-isoTQEN and 3-isoTQEN exhibit a lower-energy shift in the excitation and emission wavelengths and an enhanced fluorescence intensity, probably because of the energy-transfer mechanism between adjacent isoquinoline rings. Importantly, an increase in the Zn2+/Cd2+ discriminating ability and a reduction in the background fluorescence induced by pH were also achieved for isoquinoline derivatives. The zinc-ion-induced fluorescence of these isoTQENs was not quenched by an addition of TPEN, which demonstrates the significantly high zinc-ion binding ability of these isoTQEN ligands.
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)
Yuji Mikata, Keiko Kawata, Satoshi Iwatsuki, and Hideo KonnoInorganic Chemistry2012 51 (3), 1859-1865Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)
Yuji Mikata, Keiko Kawata, Satoshi Iwatsuki, and Hideo KonnoInorganic Chemistry2012 51 (3), 1859-1865Isoquinoline-based tetradentate ligands with C3-symmetry, tris(1- or 3-isoquinolylmethyl)amine (1- or 3-isoTQA), have been prepared and their zinc-induced fluorescence enhancement was investigated. Upon excitation at 324 nm, 1-isoTQA shows very weak ...
Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor
Zhaochao Xu, Kyung-Hwa Baek, Ha Na Kim, Jingnan Cui, Xuhong Qian, David R. Spring, Injae Shin and Juyoung YoonJournal of the American Chemical Society2010 132 (2), 601-610Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor
Zhaochao Xu, Kyung-Hwa Baek, Ha Na Kim, Jingnan Cui, Xuhong Qian, David R. Spring, Injae Shin and Juyoung YoonJournal of the American Chemical Society2010 132 (2), 601-610It is still a significant challenge to develop a Zn2+-selective fluorescent sensor with the ability to exclude the interference of some heavy and transition metal (HTM) ions such as Fe2+, Co2+, Ni2+, Cu2+, Cd2+, and Hg2+. Herein, we report a novel amide-...
Synthesis and Coordination Properties of Quinoline Pendant Arm Derivatives of [9]aneN3 and [9]aneN2S as Fluorescent Zinc Sensors
Marta Mameli, M. Carla Aragoni, Massimiliano Arca, Marta Atzori, Andrea Bencini, Carla Bazzicalupi, Alexander J. Blake, Claudia Caltagirone, Francesco A. Devillanova, Alessandra Garau, Michael B. Hursthouse, Francesco Isaia, Vito Lippolis and Barbara ValtancoliInorganic Chemistry2009 48 (19), 9236-9249Synthesis and Coordination Properties of Quinoline Pendant Arm Derivatives of [9]aneN3 and [9]aneN2S as Fluorescent Zinc Sensors
Marta Mameli, M. Carla Aragoni, Massimiliano Arca, Marta Atzori, Andrea Bencini, Carla Bazzicalupi, Alexander J. Blake, Claudia Caltagirone, Francesco A. Devillanova, Alessandra Garau, Michael B. Hursthouse, Francesco Isaia, Vito Lippolis and Barbara ValtancoliInorganic Chemistry2009 48 (19), 9236-9249The coordination chemistry of three new quinoline pendant arm derivatives of [9]aneN3 (L1, L2) and [9]aneN2S (L3) toward CuII, ZnII, CdII, HgII, and PbII has been investigated both in solution and in the solid state. The protonation constants for L1−L3 ...
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History
- Published In Issue August 18, 2008
- Article ASAPJuly 22, 2008
- Received: February 10, 2008
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