Vapor phase pH induced fluorescence switching of a dimethylaminostyryl terpyridine derivative in thin films

Vaidya, Srivathsa; Schmehl, Russell H.

doi:10.1039/c1nj20754g

Cited by 8 publications

(6 citation statements)

References 35 publications

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“…The pK a1 and pK a3 values fall within the corresponding pK a ranges of 0.31-2.48 and 8.21-9.65 that we previously reported for the acid ionization constant values of protonated imidazolium on analogous Ru(II) complexes [37][38][39][40][41][42][43][44][45]. The value of pK a2 agrees well with pK a = 3.55-4.65 for the uncoordinated peripheral pyridyl of the terpyridine on 4-phosphonato-2,2′:6′,2″-terpyridine [46] and dimethylaminostyrylterpyridine [47].…”

Section: Ph Effects On the Uv-vis Absorption And Emission Spectrasupporting

confidence: 83%

Off–on–off pH luminescence switching and DNA binding properties of a free terpyridine-appended ruthenium complex

Zheng

Kang

et al. 2014

Journal of Inorganic Biochemistry

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Section: Ph Effects On the Uv-vis Absorption And Emission Spectrasupporting

confidence: 83%

Off–on–off pH luminescence switching and DNA binding properties of a free terpyridine-appended ruthenium complex

Zheng

Kang

et al. 2014

Journal of Inorganic Biochemistry

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“…The research on the acid/base-dependent fluorescence switching of pyridine-containing chromophores has been extensively studied in solutions and amorphous films. , In comparison, there are few reports focusing on the luminescence switching of crystal structures or aggregate materials. − ,− With this in mind, we began to investigate the acid/base vapor-triggered luminescence switching of the ionic microcrystals 1 (HX) 2 . Taking 1 (HCl) 2 as an example, after being fumed by NEt 3 vapor for 5 min, the blue emission was almost quenched completely (Figure ).…”

Section: Results and Discussionmentioning

confidence: 99%

Ionic Organic Microcrystals with Bright Deep-Blue Luminescence and Acid/Base Vapor Response

Tang

et al. 2021

Crystal Growth & Design

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A new class of high-quality ionic organic microcrystals with bright deep-blue luminescence (with up to 60% quantum yield) have been prepared in situ by the protonation of 2,2′-di(pyrid-2-yl)biphenyl (1) with different proton acids (HCl, HClO4, CH3SO3H, or CF3SO3H). The obtained rod-shaped microcrystals are characterized by SEM and PXRD analyses. As a result of the deprotonation and reprotonation of the pyridine groups, the microcrystals of 1(HCl)2 show reversible blue luminescence switching in response to NEt3/HCl vapor. In addition, single crystals of the ionic salts of 1(HCl)2, 1(HClO4)2, 1(CH3SO3H)2, and 1(CF3SO3H)2 have been obtained. X-ray analyses show that the counteranions are connected to the pyridinium protons by hydrogen bonding.

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“…It is noteworthy to mention that solvent-mediated hydrogen bonding is quite possible because of increased basicity of the terpyridine nitrogens in the excited state. 24 Effect of the Signaling Moiety on Electronic Spectra. Unlike 1, both the absorption and fluorescence excitation spectra of 2 showed sharp features with prominent vibronic band peaks, indicating poor electronic communication between the terpyridine and anthracene units (Figures 4b,c and S4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…This means that the hydrogen bonding interaction observed here with methanol or ethanol is solely an excited-state phenomenon. It is noteworthy to mention that solvent-mediated hydrogen bonding is quite possible because of increased basicity of the terpyridine nitrogens in the excited state …”

Section: Resultsmentioning

confidence: 99%

Hydrogen Bonding-Induced Unique Charge-Transfer Emission from Multichromophoric Polypyridyl Ligands: Ratiometric Probing of Methanol Impurity in Commercial Biofuels

Dey

Bhattacharya

2021

ACS Sustainable Chem. Eng.

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This work is focused on utilizing fluorescent molecules for sensing the methanol content in (bio)fuels. Multichromophoric polypyridyl ligands with pyrene (1) and anthracene (2) as aryl residues have been synthesized. The twisted geometry of the probe molecules in both the solid state and aprotic solvents significantly curtails the electronic communication between the aryl moiety and pyridyl ligand (terpyridine). However, the excited-state hydrogen bonding interactions of methanol with terpyridine nitrogens result in the formation of a nearly planar conformation with larger charge separation. Thus, a broad “structureless” fluorescence spectrum was observed specifically in methanol with an exceptionally large Stokes shift (detection limit: 0.13%). However, the extent of redshift was found to be attributed to the angle of twisting as well as the electronic nature of the aryl moiety. Considering its high sensitivity, probe 1 is utilized for the detection of methanol impurity in soy-based biodiesel samples, like B100, B20, and so on. Interference studies indicate that the presence of competitive byproducts, such as monoglycerides and diglycerides, or unconsumed starting materials, such as fatty acid methyl esters poses no serious threats in methanol detection. Finally, the methanol-specific fluorescence response has been utilized to design paper strips for on-location detection of methanol contamination in biofuel samples.

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Vapor phase pH induced fluorescence switching of a dimethylaminostyryl terpyridine derivative in thin films

Cited by 8 publications

References 35 publications

Off–on–off pH luminescence switching and DNA binding properties of a free terpyridine-appended ruthenium complex

Off–on–off pH luminescence switching and DNA binding properties of a free terpyridine-appended ruthenium complex

Ionic Organic Microcrystals with Bright Deep-Blue Luminescence and Acid/Base Vapor Response

Hydrogen Bonding-Induced Unique Charge-Transfer Emission from Multichromophoric Polypyridyl Ligands: Ratiometric Probing of Methanol Impurity in Commercial Biofuels

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