Terthiophene Appended with Terpyridine Units as Receptors for Protons and Zn<sup>2+</sup> Ions: Photoinduced Energy and Electron Transfer Processes

Bergamini, Giacomo; Boselli, Luca; Ceroni, Paola; Manca, Paola; Sanna, Gavino; Pilo, Maria Itria

doi:10.1002/ejic.201100582

Cited by 11 publications

(12 citation statements)

References 21 publications

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“…Back electron transfer follows to restore compound 2 to the ground state non-radiatively. A similar explanation for fluorescence quenching of tpy-appended terthiophene by Zn II was recently reported by Ceroni and co-workers (60).…”

Section: Supramolecular Chemistry 703mentioning

confidence: 61%

Zn^II and Pb^II coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

Younes

Clark

Zhu

2012

Supramolecular Chemistry

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2012) Zn II and PbII coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of 'clickate'-appended anthracene, Supramolecular Chemistry, 24:9, 696-706,The effect of metal coordination of 2-(1-(9-anthryl)methyl-1,2,3-triazol-4-yl)-6-(1-n-octyl-1,2,3-triazol-4-yl)pyridine (2) on the emission of the appended anthryl group was investigated in acetonitrile. The tridentate 2,6-bis(1,2,3-triazol-4-yl)pyridyl ligand included in 2 is referred herein as 'clickate'. Titrating zinc(II) perchlorate or zinc(II) chloride into the solution of fluorescent ligand 2 results in quenching, which is attributed to the formation of a dark 1:1 Zn II complex of 2. Frontier molecular orbital analysis and cyclic voltammetric data support the occurrence of photoinduced electron transfer from the excited state of the anthryl group to the Zn II -bound clickate moiety, which relaxes the excited fluorophore non-radiatively, i.e. quenches fluorescence. Fluorescence quenching of clickate 2 upon forming the Pb II complex was also observed. The Zn II /Pb II -coordination chemistry of clickate was characterised via X-ray crystallography, isothermal titration calorimetry, 1 H NMR spectroscopy and absorption spectroscopy using the symmetrically substituted clickate 2,6-bis(1-n-octyl-1,2,3-triazol-4 yl)pyridine (1).

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Section: Supramolecular Chemistry 703mentioning

confidence: 61%

Zn^II and Pb^II coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

Younes

Clark

Zhu

2012

Supramolecular Chemistry

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“…Indeed, Zn(II)-bound bipy and terpyridyl ( terpy ) have been found to quench fluorescence in other cases. 85,86 …”

Section: Singlet State Ligand-centered Photophysical Processesmentioning

confidence: 99%

“…86,204,205 Zn(II)-binding lowers the LUMO level of terpy , renders it an efficient e-acceptor to provide a PET pathway for the fluorophores in 20 (Fig. 24, left), 204 TTT , 86 and 21 , 206 which contains a 1,2,3-triazolyl analogue of terpy (“clickate”), to relax non-radiatively. The clickate/Zn(II) coordination is similar to that of terpy in both coordination geometry and associated fluorescence modulations.…”

Section: Zn(ii) Coordination Chemistrymentioning

confidence: 99%

“…The clickate/Zn(II) coordination is similar to that of terpy in both coordination geometry and associated fluorescence modulations. 206 Compounds 22 205 and TAT 86 (Fig. 24, right) are ICT-type fluorophores.…”

Section: Zn(ii) Coordination Chemistrymentioning

confidence: 99%

“… Terpy -containing fluorescent ligands 20 , 204 TTT , 86 22 , 205 TAT , 86 for Zn(II) ions. Compound 21 206 contains a terpy analogue “clickate”.…”

Section: Figmentioning

confidence: 99%

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Zn(ii)-coordination modulated ligand photophysical processes – the development of fluorescent indicators for imaging biological Zn(ii) ions

et al. 2014

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Molecular photophysics and metal coordination chemistry are the two fundamental pillars that support the development of fluorescent cation indicators. In this article, we describe how Zn(II)-coordination alters various ligand-centered photophysical processes that are pertinent to developing Zn(II) indicators. The main aim is to show how small organic Zn(II) indicators work under the constraints of specific requirements, including Zn(II) detection range, photophysical requirements such as excitation energy and emission color, temporal and spatial resolutions in a heterogeneous intracellular environment, and fluorescence response selectivity between similar cations such as Zn(II) and Cd(II). In the last section, the biological questions that fluorescent Zn(II) indicators help to answer are described, which have been motivating and challenging this field of research.

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Cd(II) Complexes of 2,2':6',2''‐Terpyridine Substituted at 4'‐Position with Thienyl Groups: Synthesis, Structures, Luminescence, and Photocatalytic Activities

Zhang

Yan

2017

J Chinese Chemical Soc

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Four new complexes, namely Cd(II)(4'‐(2‐(5‐R‐thienyl))‐terpyridine)2(ClO4)2 (R = hydrogen (1), bromo (2), methyl (3), and methoxy (4)), were synthesized and characterized by high‐resolution mass spectrometry, infrared (IR) spectroscopy, and elemental analysis. Complexes 2 and 4 were further characterized by single‐crystal X‐ray diffraction analysis, which showed that the Cd(II) ions in complexes 2 and 4 are both six‐coordinated with the N6 coordination sphere, displaying distorted octahedral geometries. The luminescence of complexes 1–4 was studied. Moreover, the photocatalytic properties of complexes 1–4 were investigated and compared with those of their parent complex Cd(II)(terpyridine)2(ClO4)2.

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Terthiophene Appended with Terpyridine Units as Receptors for Protons and Zn²⁺ Ions: Photoinduced Energy and Electron Transfer Processes

Cited by 11 publications

References 21 publications

Zn^II and Pb^II coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

Zn^II and Pb^II coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

Zn(ii)-coordination modulated ligand photophysical processes – the development of fluorescent indicators for imaging biological Zn(ii) ions

Cd(II) Complexes of 2,2':6',2''‐Terpyridine Substituted at 4'‐Position with Thienyl Groups: Synthesis, Structures, Luminescence, and Photocatalytic Activities

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Terthiophene Appended with Terpyridine Units as Receptors for Protons and Zn2+ Ions: Photoinduced Energy and Electron Transfer Processes

Cited by 11 publications

References 21 publications

ZnII and PbII coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

ZnII and PbII coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

Zn(ii)-coordination modulated ligand photophysical processes – the development of fluorescent indicators for imaging biological Zn(ii) ions

Cd(II) Complexes of 2,2':6',2''‐Terpyridine Substituted at 4'‐Position with Thienyl Groups: Synthesis, Structures, Luminescence, and Photocatalytic Activities

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Terthiophene Appended with Terpyridine Units as Receptors for Protons and Zn²⁺ Ions: Photoinduced Energy and Electron Transfer Processes

Zn^II and Pb^II coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene

Zn^II and Pb^II coordination chemistry of 2,6-bis(1,2,3-triazol-4-yl)pyridine (clickate) and the metal ion-dependent emission of ‘clickate’–appended anthracene