Naphthalenyl- and anthracenyl-ethynyl dT analogues as base discriminating fluorescent nucleosides and intramolecular energy transfer donors in oligonucleotide probes

Xiao, Qiang; Ranasinghe, Rohan T.; Tang, A.; Brown, Tom

doi:10.1016/j.tet.2006.10.090

Cited by 56 publications

(42 citation statements)

References 25 publications

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“…With respect to the synthesis of the compounds, CuAAC of azido‐functionalized N ‐phenylaza‐[18]crown‐672, 77, 78 with N ‐( n ‐butyl)‐4‐ethinyl‐1,8‐naphthalimide,79 4,4‐difluoro‐8‐(4‐ethinylphenyl)‐1,3,5,7‐tetramethyl‐4‐bora‐3a,4a‐diaza‐ s ‐indacene80–83 and 9‐ethinyl‐anthracene84 afforded 1 , 6 and 7 . The respective reaction of ethinyl‐functionalized N ‐phenylaza‐[18]crown‐672, 85 with 6‐azido‐ N ‐ethyl‐1,8‐naphthalimide,62 9‐azidomethyl‐anthracene,86 9‐azidomethyl‐10‐cyanoanthracene,86, 87 and 9‐azidomethyl‐10‐methylanthracene86, 88 yielded 2 – 5 .…”

Section: Resultsmentioning

confidence: 99%

Integration of the 1,2,3‐Triazole “Click” Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes

Ast

Fischer

Müller

et al. 2013

Chemistry A European J

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In a systematic approach we synthesized a new series of fluorescent probes incorporating donor-acceptor (D-A) substituted 1,2,3-triazoles as conjugative π-linkers between the alkali metal ion receptor N-phenylaza-[18]crown-6 and different fluorophoric groups with different electron-acceptor properties (4-naphthalimide, meso-phenyl-BODIPY and 9-anthracene) and investigated their performance in organic and aqueous environments (physiological conditions). In the charge-transfer (CT) type probes 1, 2 and 7, the fluorescence is almost completely quenched by intramolecular CT (ICT) processes involving charge-separated states. In the presence of Na(+) and K(+) ICT is interrupted, which resulted in a lighting-up of the fluorescence in acetonitrile. Among the investigated fluoroionophores, compound 7, which contains a 9-anthracenyl moiety as the electron-accepting fluorophore, is the only probe which retains light-up features in water and works as a highly K(+)/Na(+)-selective probe under simulated physiological conditions. Virtually decoupled BODIPY-based 6 and photoinduced electron transfer (PET) type probes 3-5, where the 10-substituted anthracen-9-yl fluorophores are connected to the 1,2,3-triazole through a methylene spacer, show strong ion-induced fluorescence enhancement in acetonitrile, but not under physiological conditions. Electrochemical studies and theoretical calculations were used to assess and support the underlying mechanisms for the new ICT and PET 1,2,3-triazole fluoroionophores.

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Section: Resultsmentioning

confidence: 99%

Integration of the 1,2,3‐Triazole “Click” Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes

Ast

Fischer

Müller

et al. 2013

Chemistry A European J

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“…Molecule 1 was synthesized as follows: 9-ethynylanthracene [11] (1.1 g, 5 mmol), 9-bromoanthracene (1.4 g, 5.5 mmol), Pd(PPh 3 ) 2 Cl 2 (105 mg, 0.15 mmol), and CuI (57 mg, 0.30 mmol) were added to a 250 mL three-necked flask, and the mixture was thoroughly degassed with highly-pure N 2 three times. Then, THF (150 mL) and pipyridine (10 mL) were injected in one portion.…”

Section: Methodsmentioning

confidence: 99%

Organic Single‐Crystalline Ribbons of a Rigid “H”‐type Anthracene Derivative and High‐Performance, Short‐Channel Field‐Effect Transistors of Individual Micro/Nanometer‐Sized Ribbons Fabricated by an “Organic Ribbon Mask” Technique

et al. 2008

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“…Tetrakis(triphenylphosphine)palladium(0) (99.8%), CuI (98%), Alfa Aesar; 1,1´‐bis(diphenylphosphino) ferrocene (DPPF, 99%), Strem Chemicals. anthracen‐9‐ylboronic acid and 9‐ethynylanthracene were synthesized according to the literature procedures. Other reagents were all purified with standard methods if needed.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of blue luminescent bipolar materials constructed with carbazole and anthracene units with 4‐cyanophenyl substitute at the 9‐position of the carbazole unit

Xie¹,

Yuan²,

Li³

et al. 2018

Luminescence

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With carbazole and p-cyanobromobenzene as raw materials, 4-(3,6-di (anthracen-9-yl)-9H-carbazol-9-yl)benzonitrile (DACB) and 4-(3,6-bis(anthracene -9-ylethynyl)-9H-carbazol-9-yl)benzonitrile (BACB) were synthesized through the Suzuki coupling reaction and the Sonogashira coupling reaction, respectively. These structures were characterized using H nuclear magnetic resonance (NMR), elemental analysis and mass spectrometry. Their thermal properties, ultraviolet-visible (UV-vis) absorption, fluorescence emission, fluorescence quantum yields and electrochemical properties were also investigated systematically. In addition, a electroluminescence (EL) device was made with BACB as the emitting layer and performance of the EL device was studied. Results showed that: (1) the temperature points with 5% and 10% of DACB weight loss were 443°C and 461°C, respectively, and were 475°C and 506°C with BACB weight loss of 5% and 10%, respectively. When the temperature was 50-300°C, no significantly thermal transition was observed which suggested that they had excellent thermal stability. (2) DACB and BACB had single emission peaks at 415 nm, and 479 nm with fluorescence quantum yields of 0.61 and 0.87, respectively, indicating that both compounds could emit strong blue light. (3) According to electrochemical measurement on BACB and DACB, their gaps were 3.07 eV and 2.76 eV, respectively, which further showed that these two compounds were very stable and acted as efficient blue light materials. (4) The turn-on voltage of the device was 5 V, and the device emitted dark blue light with Commission Internationale de L'Eclairage (CIE) coordinates of (0.157, 0.079).

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Naphthalenyl- and anthracenyl-ethynyl dT analogues as base discriminating fluorescent nucleosides and intramolecular energy transfer donors in oligonucleotide probes

Cited by 56 publications

References 25 publications

Integration of the 1,2,3‐Triazole “Click” Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes

Integration of the 1,2,3‐Triazole “Click” Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes

Organic Single‐Crystalline Ribbons of a Rigid “H”‐type Anthracene Derivative and High‐Performance, Short‐Channel Field‐Effect Transistors of Individual Micro/Nanometer‐Sized Ribbons Fabricated by an “Organic Ribbon Mask” Technique

Synthesis and properties of blue luminescent bipolar materials constructed with carbazole and anthracene units with 4‐cyanophenyl substitute at the 9‐position of the carbazole unit

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