Syntheses and photophysical properties of some 4‐arylpyridinium salts

Kelley, Charles J.; Ansu, Kwabena; Budisusetyo, Wiranto; Ghiorghis, Alem; Qin, Yuanxi; Kauffman, Joel M.

doi:10.1002/jhet.5570380102

Cited by 29 publications

(19 citation statements)

References 20 publications

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“…The synthesis in the same manner, but with hexadecyloxy chains resulted in the production of pure 9,10-bis(4-hexadecyloxyphenyl)anthracene (11). 4-Ethynyl-4′octyloxybiphenyl and 9,10-dibromoanthracene were synthesised via literature methods [10,12,13]. These two reactants were combined in a Sonogashira reaction to produce 9,10-bis(4′-octyloxybiphenyl-4-ylethynyl)anthracene (12).…”

Section: Scheme 3 Synthesis Of 910-bis(4-octyloxyphenylethynyl)anthrmentioning

confidence: 99%

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Sidechain engineering in anthracene derivatives: towards photofunctional liquid crystals

Kerkhof

Allan

McGrath

et al. 2017

IJNT

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A series of anthracene derivatives were synthesised to explore how their sidechain configurations influenced their phase behaviour and thereby guiding the design of photofunctional liquid crystalline materials. In the case of 9,10-diphenylanthracene derivatives, longer and more alkyl sidechains resulted in lower melting temperatures, yet liquid crystallinity was not observed. A novel room-temperature molecular liquid was synthesised based on 9,10-diphenylanthracene, the optical properties of which may be exploited in photonic applications. Liquid crystallinity was observed in one of the derivatives of 9,10-bis(phenylethynyl)anthracene, forming a nematic phase at around 210°C. These results highlight the potential opportunities for photofunctional materials with enhanced properties if liquid crystalline anthracenes can be found with lower phase transition temperatures.

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Section: Scheme 3 Synthesis Of 910-bis(4-octyloxyphenylethynyl)anthrmentioning

confidence: 99%

“…There are very few examples of stable π-conjugated liquids [15][16][17]. This novel material could be exploited in photonic applications including upconversion, as it retains the flow of a liquid and enables diffusion through solution in a condensed state [12].…”

Section: Phase Behaviourmentioning

confidence: 99%

Sidechain engineering in anthracene derivatives: towards photofunctional liquid crystals

Kerkhof

Allan

McGrath

et al. 2017

IJNT

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“…1,4´´´-Diaza-4,1´:4´,1´´:4´´,1´´´-quaterphenylene (PYP2) [203][204][205] Under argon atmosphere 4,4´-biphenyldiboronic acid bis(neopentyl glycol)ester (361 mg, 1.3 mmol), 4-iodpyridine (560 mg, 2.7 mmol, 2.1 equivalents), cesium fluoride (790 mg, 5.2 mmol, 4 equivalents) and tetrakis(triphenylphosphine)-palladium(0) (45 mg, 0.039 mmol, 3 mol%) were dissolved in 60 ml abs. tetrahydrofurane and refluxed for 50 hours.…”

Section: Symmetrically Functionalised Para-quaterphenylenesmentioning

confidence: 99%

Organic Molecular Nanotechnology

Schiek

Balzer

Al‐Shamery

et al. 2008

Small

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Zur Homepage der Dissertation AbstractFormation of needle-like crystals from inorganic as well as from organic semiconductors such as para-phenylenes, α-thiophenes and phenyl-thiophene co-oligomers on dielectric surfaces has attracted increasing interest within the last years. The para-hexaphenylene has proven to be a versatile building block for generating long, parallely aligned organic nanofibers by a self-assembly process on a muscovite mica substrate via sublimation in high vacuum. These nanofibers possess outstanding optical properties like strong, polarised blue fluorescence in high quantum yields after unpolarised excitation with UV light, waveguiding and lasing features. Furthermore, they are chemically and thermically stable and can be easily detached from the growth substrate to serve as key elements in next generation optoelectronic and nanophotonic devices. Owing to their typical height and width on a nanometer scale and length up to one millimeter, the fibers bridge the gap between microscopic and macroscopic dimensions. The morphology of the nanofibers (length, height, width, aspect ratio, bending into rings) is susceptable to process parameters and pretreatment of the substrate. But chemically functionalisation of the molecular building block as key step of this thesis widens the scope of possibilities: Nanoaggregates with tailored morphology and optical properties are generated from designed functionalised molecular building blocks. Functional groups have been implemented at the 1,4´´´-para-positions of p-quaterphenylenes using a non-trivial Suzuki cross-coupling strategy. Symmetrically as well as non-symmetrically functionalised oligomers have been achieved in excellent yields and high purity. Additionally, the synthesis of phenyl-thiophene cooligomers and their acceptability for the nanofiber growth on muscovite mica via organic molecule deposition in high vacuum are presented. The fluorescence peak emission frequency of the nanostructures from the substituted p-quaterphenylenes shifts within the blue depending on the functionalisation. While dimensions are still influenced by the growth parameters, the overall shape (i.e. cross-section) of the aggregates alters significantly with the functional group. Even new properties like nonlinear optical activity are accessible. Due to intrinsic nonzero hyperpolarisability of push-pull functionalised oligomers, the respective nanofibers act as frequency doublers and emit strong second harmonic light after excitation with near infrared femtosecond laser pulses. Note that this design approach is possible while conserving the concept of highly crystalline nanofibers. Thus, a new route of bottom-up nanotechnology is presented starting from organic molecular synthesis towards generating of tailormade organic nanofibers opening new prospects for future nanotechnology. 3 ZusammenfassungDie Bildung von nadelförmigen Kristallen aus anorganischen und organischen Halbleitermolekülen wie zum Beispiel para-Phenylenen, α-Thiophenen und Phenylthiophen Co-oligomeren fa...

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“…The electron-donating ability of amines is inverted upon protonation or quaternization, particularly the pyridinium ion is a common acceptor unit [24, 25], but ammonium ions have also received considerable attention [26]. The influence of environmental conditions on the electron donating or accepting capability of amino groups and azines can be used to alter the optical properties of a chromophore by tuning the strength of the nitrogen-containing donor (amines) and acceptor (azines) groups.…”

Section: Introductionmentioning

confidence: 99%

Linear and Angular Distyrylpyrazines with Terminal Donor Groups: Synthesis, Solvatochromism, and Acidochromism of the Electronic Spectra

Schmitt

Fischer

Detert

2011

ISRN Organic Chemistry

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A series of linear and angular distyrylpyrazines and lateral donor groups has been prepared by aldol condensation between dimethylpyrazines and the appropriate aromatic aldehyde. The optical absorption and emission properties of these systems were studied in different solvents and media. The materials display a strong solvatochromism of the emission that is reflected by large red shifts of their fluorescence emission maxima on increasing the solvent polarity. This behaviour suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. Upon protonation, the UV-vis spectra are altered, and the fluorescence intensity of the neutral compound vanishes. These molecules can be used as colorimetric and luminescence polarity and pH sensors.

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Syntheses and photophysical properties of some 4‐arylpyridinium salts

Cited by 29 publications

References 20 publications

Sidechain engineering in anthracene derivatives: towards photofunctional liquid crystals

Sidechain engineering in anthracene derivatives: towards photofunctional liquid crystals

Organic Molecular Nanotechnology

Linear and Angular Distyrylpyrazines with Terminal Donor Groups: Synthesis, Solvatochromism, and Acidochromism of the Electronic Spectra

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