2,5-bis(Arylethynyl)thienyl systems: Preparation and photophysical properties. Part II

Coombs, Benjamin A.; Rutter, Simon R.; Goeta, Andrés E.; Sparkes, Hazel A.; Batsanov, Andrei S.; Beeby, Andrew

doi:10.1039/c1ra00728a

Cited by 16 publications

(10 citation statements)

References 47 publications

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Section: Introductionmentioning

confidence: 99%

“…In our design of the new compounds, we combined the favourable fluorescencei ncrease upon binding to DNA and RNA observedf or the bithiophene 1 with the two triple bonds, responsible for the strong Ramans ignal of compound 2,w hich led to compound 3 (Figure 2), resembling 2,5-bis(phenylethynyl)thiophene (BPET) chromophores investigated by our group and others. [107,108] For comparison, ar eferencec ompound in the form of the 1,4-phenylene analogue 4 was prepared, ab is-(phenylethynyl)benzene (BPEB) derivative [109][110][111][112][113][114][115] in whicht he overall length of the linker is somewhat shorter than in compound 3.T he bis(phenylethynyl)anthracene( BPEA)d erivative 5,w as chosen because BPEAs are strongf luorophores [116][117][118][119][120][121][122][123] and the long axis of anthracenei nc ompound 5 is perpendicular to the bis-triarylborane longitudinal axis. Such an orientation of al arge and rigid aromatic moiety is expected to have a significant effecto nt he nature of the binding interactions with DNA/RNA.…”

Section: Introductionmentioning

confidence: 99%

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Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Ferger

Ban

Krošl

et al. 2021

Chemistry A European J

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We report four new luminescent tetracationic bis‐triarylborane DNA and RNA sensors that show high binding affinities, in several cases even in the nanomolar range. Three of the compounds contain substituted, highly emissive and structurally flexible bis(2,6‐dimethylphenyl‐4‐ethynyl)arene linkers (3: arene=5,5′‐2,2′‐bithiophene; 4: arene=1,4‐benzene; 5: arene=9,10‐anthracene) between the two boryl moieties and serve as efficient dual Raman and fluorescence chromophores. The shorter analogue 6 employs 9,10‐anthracene as the linker and demonstrates the importance of an adequate linker length with a certain level of flexibility by exhibiting generally lower binding affinities than 3–5. Pronounced aggregation–deaggregation processes are observed in fluorimetric titration experiments with DNA for compounds 3 and 5. Molecular modelling of complexes of 5 with AT‐DNA, suggest the minor groove as the dominant binding site for monomeric 5, but demonstrate that dimers of 5 can also be accommodated. Strong SERS responses for 3–5 versus a very weak response for 6, particularly the strong signals from anthracene itself observed for 5 but not for 6, demonstrate the importance of triple bonds for strong Raman activity in molecules of this compound class. The energy of the characteristic stretching vibration of the C≡C bonds is significantly dependent on the aromatic moiety between the triple bonds. The insertion of aromatic moieties between two C≡C bonds thus offers an alternative design for dual Raman and fluorescence chromophores, applicable in multiplex biological Raman imaging.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Ferger

Ban

Krošl

et al. 2021

Chemistry A European J

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“…For freely rotating ethynylene-containing systems, freezing of the sample in a rigid organic glass [5:5:2 diethyl ether/isopentane/ethanol (EPA), which is transparent at 77 K] can enable measurement of the favored planar state as the lowest-energy conformation is annealed. The rigidity of the frozen sample also serves to lower the rates of internal conversion (IC), intersystem crossing (ISC), and collisional quenching and nominally increases the rates of radiative emission and also in some cases phosphorescence …”

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confidence: 99%

Twisted Tethered Tolanes: Unanticipated Long-Lived Phosphorescence at 77 K

et al. 2013

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Influencing the communication within a conjugated system as diphenylacetylene is a challenging subject in molecular electronics. Some examples of twisted tolanes are known, where high twists have been achieved in the solid state by steric encumbrance. The insertion of a spacer system is an alternative way to tailor rotation. Only a few examples of such tethered tolanes exist, and they all suffer from small twist angles (<35°). We report on tolanophanes containing a malonyl tether, where twist angles of almost 80° were reached. Long-lived phosphorescence (4 s at 77 K) was recorded, and quantum-chemical calculations were performed to confirm the experimental results.

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“…There is a general interest in stabilized acenes as potentially useful charge transporting materials, , particularly those with electron poor aromatic cores . Trialkylsilylethynylation (e.g., TIPSA: triisopropylsilylacetylene) dramatically stabilizes acenes and heteroacenes and at the same time renders their solid state structure predictable. , Mutagenesis of the molecular structure of electron-poor acenes is critical for rational development of novel materials with desirable molecular and solid-state properties.…”

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confidence: 99%

From Thia- to Selenadiazoles: Changing Interaction Priority

et al. 2013

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The synthesis, optical, and electrochemical properties as well as solid-state structures of a series of alkynylated, benzannulated selenadiazoles are reported. This set of compounds is compared to the lighter homologue series, the thiadiazoles. The selenadiazoles show head-to-head dimerization in the solid state, while packing of the thiadiazoles was dominated by the steric bulk of the side groups. The Se-N interaction is a supramolecular motif that should drive the effective self-assembly and modulate charge transport when these compounds are used as thin films in devices.

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2,5-bis(Arylethynyl)thienyl systems: Preparation and photophysical properties. Part II

Cited by 16 publications

References 47 publications

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Twisted Tethered Tolanes: Unanticipated Long-Lived Phosphorescence at 77 K

From Thia- to Selenadiazoles: Changing Interaction Priority

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