Studies on the fluorescence properties of meso-substituted amidoanthracenes

Werner, Tobias; Rodgers, Julie

doi:10.1016/0047-2670(86)85007-9

Cited by 19 publications

(4 citation statements)

References 16 publications

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“…We have also studied the effect of varying the number of ethylenoxy units on the binding ability of metal ions in the presence of 9-anthracenecarbonamide . Since Bazilevskaya et al. , reported anomalous photochemical behavior of 9-anthracenecarboxylic acid (9-ACOOH), this subject has been the topic of discussion for many years. − Despite the interesting behavior shown by 9-ACOOH and its amide derivatives, the utilization as chemical sensors of 9-ACOOH derivatives is rather limited. , With this in mind, we examined the photophysical properties of the 9-ACOOH amide derivatives with the hope of widening this field of study. As a result, we recognized that fluorescence emission of 9-anthracene aromatic amide (9-AA) derivatives was almost quenched in solution whereas their crystal showed green-yellow-colored emission under UV irradiation.…”

Section: Introductionmentioning

confidence: 99%

New Fluorescent “Off−On” Behavior of 9-Anthryl Aromatic Amides through Controlling the Twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions

2001

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New fluorophores based on linear polyether N,N′-[oxybis(3-oxapentamethylenoxy)-2-phenyl]bis(9-anthracenecarbonamide) (3) and its analogues (2 and 4) have been synthesized, and their complexation properties with various alkali-metal and alkaline-earth-metal ions were investigated by fluorescence, UV, and 1 H NMR spectroscopies. In the absence of metal ion, 2-4 showed almost no fluorescence emission (fluorescence quantum yield Φ ) 0.0003, fluorescence "off" state) since twisted intramolecular charge transfer (TICT) occurred through the amide bond. However, 2-4 demonstrated a significant increase in fluorescence intensity around 430 nm upon complexation with alkaline-earth-metal ions. In the case of 4‚Ca 2+ , a large enhancement effect on the fluorescence quantum yield (Φ ) 0.014, [Ca 2+ ]/[4] ) 5, Φ 4‚Ca 2+ /Φ free 4 ) 42, fluorescence "on" state) was observed. This "off-on" fluorescence characteristic was originated from the cooperative strong binding mode between the carbonyl group and the ethylenoxy moiety for alkaline-earth-metal ions, resulting in effective inhibition of photoinduced TICT relaxation. Fluorophores 2-4 formed a 1:1 complex (the order of the complex formation constants was Ca 2+ > Sr 2+ ≈ Ba 2+ ) and showed no considerable spectral changes upon complexation with alkali-metal ions and Mg 2+ . The 1 H NMR study on 2-4 and their complexes indicated that free 2-4 formed a helical structure. After complexation, the conformational change of 2 from a helical structure to a semicircular structure was observed. The pseudocyclic form was supported as the complex structure of 3, whereas the large conformational change of 4 was not observed after the addition of metal ions.

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Section: Introductionmentioning

confidence: 99%

New Fluorescent “Off−On” Behavior of 9-Anthryl Aromatic Amides through Controlling the Twisted Intramolecular Charge Transfer Relaxation Process by Complexation with Metal Ions

2001

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“…Fluorescence spectra (λ exc = 365 nm) were obtained from 0.8 μM solutions of E- 1 and Z -1 in CH 2 Cl 2 , CH 3 CN, CH 3 OH, and DMF (Figure ). A remarkable 200:1 intensity ratio between the trans and cis shuttles (∼85:1 between Z - 1 and the PSS) is observed for the CH 2 Cl 2 solutions at the maximum of E - 1 emission (λ max = 417 nm), Z -1 's fluorescence being almost completely quenched by the pyridinium units and strongly red-shifted (Supporting Information) by intercomponent hydrogen bonding of the anthracene carboxyamide group to the macrocycle. 4d,, The emission spectra in the various solvents show an increase in Z -1 luminescence with increasing hydrogen bond basicity 10 (CH 2 Cl 2 < CH 3 CN < CH 3 OH < DMF), consistent with a reduction in positional integrity of the macrocycle at the GlyGly station as the intercomponent hydrogen bonds are weakened. Conversely, the fluorescence intensity of E -1 generally decreases with this trend (opposite to the normally observed polarity effects on electron transfer and excited-state relaxation processes) as the macrocycle increasingly spends time away from the fumaramide station in positions within efficient quenching distance of the anthracene.…”

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confidence: 97%

A Generic Basis for Some Simple Light-Operated Mechanical Molecular Machines

et al. 2004

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A novel type of mechanical switch is described in which light-induced translation of a macrocycle in a [2]rotaxane quenches anthracene fluorescence. Features of the system include the remarkable 200:1 difference in fluorescence intensity between the two positional states of the molecule ( approximately 85:1 between one isomer and the photostationary state). In principle the same concept could be used for mechanically switching virtually any property that can be influenced by functional group proximity effects.

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“…The fluorescence of anthracene-9-carboxamide has been studied by Werner and Rogers, who observed that the spectrum is broadened and red-shifted in the strongly hydrogen bond donating solvent 2,2,2-trifluoroethanol. The thread 2 shows the same effect (Figure ).…”

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confidence: 99%