Cation complexation behavior of pyrene- and anthracene-appended new crown ether derivatives

Wang, Zhiping; Chang, Seung Hyun; Kang, Tai-Jong

doi:10.1016/j.saa.2007.08.006

Cited by 14 publications

(16 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These types of sensors can be roughly categorized into three groups based on their response to metal ions. The first two sensor groups are those that undergo turn-ON (17)(18)(19)(20)(21)(22)(23)(24) or turn-OFF responses (25)(26)(27) typically caused by the removal or installation of photoinduced electron transfer (PET) or heavy atom effect promoted quenching pathways. In the third group, sensing is based on monomer/excimer emission switching (28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43) induced by changes in spatial distances between two pyrene moieties.…”

Section: Introductionmentioning

confidence: 99%

“…In the third group, sensing is based on monomer/excimer emission switching (28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43) induced by changes in spatial distances between two pyrene moieties. Moreover, the pyrene and crown ether groups in these types of sensors are normally linked by flexible chains, such as methylene (17)(18)(19)(20)(21)28,29,(44)(45)(46), ether (30,47,48), oligoethylene glycol (31)(32)(33)(34), ester (22), amine (49), amide (25)(26)(27)(35)(36)(37)(38)(39)(40)(41)50), imine (23), triazole (51), sulfoxide (24) and DNA…”

Section: Introductionmentioning

confidence: 99%

“…Pyrene and its derivatives are often used as fluorescent materials owing to several advantageous features including photochemical inertness, dual fluorescence (monomer/excimer) and high emission quantum yield . Thus far, many substances containing linked pyrenes and crown ethers have been designed to serve as fluorescent metal ion sensors . These types of sensors can be roughly categorized into three groups based on their response to metal ions.…”

Section: Introductionmentioning

confidence: 99%

“…In the third group, sensing is based on monomer/excimer emission switching induced by changes in spatial distances between two pyrene moieties. Moreover, the pyrene and crown ether groups in these types of sensors are normally linked by flexible chains, such as methylene (), ether , oligoethylene glycol , ester , amine , amide (), imine , triazole , sulfoxide and DNA units. As a consequence, decreases in fluorescence efficiencies by thermal (nonradiative) decay pathways arising from molecular motion are inevitable.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Maeda

Tanaka

Aratani

et al. 2019

Photochem & Photobiology

View full text Add to dashboard Cite

Substances containing ethynylpyrenes linked to either one or four benzocrown ethers were synthesized, and their absorption and fluorescence spectroscopic responses to metal ions were assessed. Addition of metal perchlorates to solutions of these substances promotes short wavelength shifts in their absorption and fluorescence maxima and increases in their fluorescence intensities. The magnitudes of the fluorescence intensity increases are dependent on the ring size and number of the crown ether and the nature of the metal cation. Association constants for complex formation were calculated using fluorescence intensity versus concentration data. Analysis using Job's plots showed that the substances containing one benzocrown ether moiety form 1:1 complexes with metal ions. Results of experiments employing repeated addition and removal of Mg(ClO4)2 demonstrate that the ON‐OFF fluorescence response can be repeated at least three times. Results of molecular orbital calculations show that complexation with metal ions lowers the energies of both the π and π* levels of the ethynylpyrene moiety and that in some cases the vacant orbital on the metal becomes the LUMO of the complex. An explanation of the spectroscopic changes promoted by metal ions is proposed in terms of electrostatic repulsion and structural regulation.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Maeda

Tanaka

Aratani

et al. 2019

Photochem & Photobiology

View full text Add to dashboard Cite

show abstract

“…Crown ethers have been used as a recognition moiety in fluorescent chemosensors [22][23][24][25][26]. The structure having p-conjugation systems such as pyrene, anthracene, dansyl, and coumarine has been used as signaling moiety.…”

Section: Introductionmentioning

confidence: 99%

Azathia crown ethers carrying pyrene pendant as receptor molecules for metal sensor systems

Ocak¹,

Ocak²,

Parlayan³

et al. 2011

Journal of Luminescence

View full text Add to dashboard Cite

A Ratiometric Luminescent Switch Based on Platinum Complexes Tethered to a Crown‐Ether Scaffold

et al. 2016

View full text Add to dashboard Cite

A ratiometric chemosensor for potassium is reported, based on phosphorescent dinuclear cyclometalated Pt(II) complexes featuring a cis-crown ether as the cation-recognition unit. The metal complexes are blue luminescent in a non-aggregated state but become strongly orange emissive when in a close physical proximity, as is the case when the macrocycle is in the folded state. Upon binding of the cation, unfolding occurs, resulting in a pronounced change in the emission properties (e.g. emission wavelength), which can be used for ratiometric sensing applications. The reversibility of the binding was confirmed by competitive titration experiments with unsubstituted 18-crown-6; the system shows supramolecular switching behavior.

show abstract

Cation complexation behavior of pyrene- and anthracene-appended new crown ether derivatives

Cited by 14 publications

References 20 publications

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Azathia crown ethers carrying pyrene pendant as receptor molecules for metal sensor systems

A Ratiometric Luminescent Switch Based on Platinum Complexes Tethered to a Crown‐Ether Scaffold

Contact Info

Product

Resources

About