The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry

Sheepwash, Erin; Rowntree, P.; Schwan, Adrian L.

doi:10.1002/jlcr.1541

Cited by 4 publications

(3 citation statements)

References 29 publications

(70 reference statements)

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“…For flash chromatography, Merck silica gel 32–63 μm was used. 5-Brom-2,3,3-trimethyl-3 H -indole, triethylammonium 2-butoxy-3-(dicyanomethylene)-4-oxocyclobut-1-enolate ( CN ), 3,7-dimethyloctyl tosylate, 2 , and mSQ2 were synthesized according to the given literature.…”

Section: Methodsmentioning

confidence: 99%

Exciton Coupling Effects in Polymeric cis-Indolenine Squaraine Dyes

Völker¹,

Lambert²

2012

Chem. Mater.

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Dicyanovinylene-substituted cis-indolenine squaraines were polymerized by a Ni-mediated Yamamoto homocoupling reaction. Preparative recycling GPC was used to obtain polymer fractions with different molecular weight distributions in order to investigate the influence of molecular weight on the optical properties. In this attempt, conjugated cyclic trimers could also be isolated that are, to the best of our knowledge, the first of their kind. These trimers and the squaraine polymers were investigated by cyclic voltammetry, absorption spectroscopy, and static and time-resolved fluorescence spectroscopy. While the trimers show multiple fluorescence bands with, for squaraines, an exceptional huge Stokes' shift, the polymers show broad absorption in the red to near infrared (NIR) region with narrow fluorescence and only the common minor Stokes' shift. The spectral features of the squaraines were interpreted to be caused by excitonic coupling. By comparison of experimental and computed (CNDO/S2 CIS) spectra detailed, structural models of the polymers were derived that consist of helix (H-aggregate behavior) and zigzag motifs (Jaggregate behavior). ■ INTRODUCTIONThe goal of this work is to synthesize polysquaraine dyes that are based on dicyanovinylene indolenine squaraine monomers and to study their optical and electrochemical properties. Squaraines (Scheme 1) are intensely colored dyes that are generated by 1,3-dicondensation reactions of nucleophilic compounds such as heterocycles or other electron-rich aromatics with squaric acid. This results in a donor− acceptor−donor structure with a strong and narrow cyaninelike absorption (ε > 10 5 M −1 cm −1 ) and fluorescence in the red to near-infrared (NIR) region. These unique absorption and fluorescence properties make squaraines suitable for a variety of applications in nonlinear optics, 1−7 data imaging, 8 organic photovoltaics, 9−17 or as fluorescence labels 18−21 and sensors for anions, 22 cations, 23−27 and neutral molecules. 28,29 There are several highly recommended reviews that give more-detailed insight into this remarkable class of dye. 30−33 The absorption maximum of squaraine dyes can be influenced by the nucleophilic component (e.g., anilines, pyrroles, indolenines and its heteroatom analogues), by replacing one oxygen of squaric carbonyl group by, e.g., sulfur 34,35 or methylene active moieties, such as dicyanomethylene 9,34,36 or barbituric acid, 34 and finally by adding electron-donating substituents to the nucleophilic (hetero)cycle component. We recently investigated the latter aspect, using triarylamine substituents attached to a series of indolenine squaraine dyes. 37 These triarylamine−squaraine conjugates display a bathochromic shift of the absorption maximum and versatile redox behavior. A totally different way to shift the absorption of squaraine dyes is to synthesize oligomers or polymers that then show band shifts and broadenings due to excitonic coupling of localized squaraine states. In this context, we recently prepared polymers based on indo...

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Section: Methodsmentioning

confidence: 99%

Exciton Coupling Effects in Polymeric cis-Indolenine Squaraine Dyes

Völker¹,

Lambert²

2012

Chem. Mater.

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“…36 1,1,2,2,3,3,4,4-Octadeutero-4-iodobutan-1-ol (2*). 37 Prepared in a similar fashion to 1, using d 8 -THF (0.80 g, 10.0 mmol), BF 3 •OEt 2 (2.84 g, 20.0 mmol), and NaI (3.00 g, 20.0 mmol) in dry MeCN (20 mL). The iodide 2* was isolated as a yellow oil (2.00 g, 96%).…”

Section: ■ Conclusionmentioning

confidence: 99%

Isotope-Coded Maleimide Affinity Tags for Proteomics Applications

et al. 2021

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Isotope-coded affinity tags (ICATs) are valuable tools for mass spectrometry-based quantitative proteomics, in particular, for comparison of protein (cysteine-residue) thiol oxidation state in normal, stressed, and diseased tissue. However, the iodoacetamido electrophile used in most commercial ICATs suffers from poor thiolselectivity and modest rates of adduct formation, which can lead to spurious results. Hence, we designed and synthesized three ICATs containing thiol-selective N-alkylmaleimide electrophiles (isotopecoded maleimide affinity tags = ICMATs) and assessed these as mass spectrometry probes for ratiometric analysis of lysozyme and muscle proteomes. Two ICMAT pairs containing butylene/D 8 -butylene linkers were effective MS probes, but not ideal for typical proteomics workflows, because peptides bearing these tags frequently did not coelute with HPLC. A switch to a phenylene/ 13 C 6 -phenylene linker solved this issue without compromising the efficiency of adduct formation.

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“…The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.langmuir.4c00012. Determination of Blue acid dissociation constants; form factor models used to interpret SANS curves; details on fits to full contrast SANS curves; impact dependence of solution pD on C 12 E 5 self-assembly; evaluation of light scattering data; isotope effects; light scattering from BlueH/C 12 E 5 solutions at pD = 2; determination of the SANS match point of C 12 E 5 in D 2 O; NMR spectra; comparison of parameters from full contrast and C 12 E 5 contrast matched SANS; and synthesis of deuterated C 12 E 5 . The authors have cited additional references within the Supporting Information. − (PDF) …”

mentioning

confidence: 99%

Impact of Additive Hydrophilicity on Mixed Dye-Nonionic Surfactant Micelles: Micelle Morphology and Dye Localization

Müller,

Sroka,

Schweins

et al. 2024

Langmuir

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The nonionic surfactant pentaethylene glycol-monododecylether C 12 E 5 forms micelles in aqueous solutions with a lower critical solution temperature. This characteristic solution behavior of C 12 E 5 is independent of the pH. Such micelles are used to solubilize a large variety of active guest molecules like for instance dyestuffs. An example is an acidic azo dye termed Blue used as a hair colorant. Depending on the pH, Blue gradually changes its hydrophilicity from the protonated BlueH at pH = 2 to the bivalent anion Blue 2− at pH = 13 while keeping the shape and size of Blue essentially unchanged. These features of C 12 E 5 and Blue offer the unique chance to investigate the sole impact of a tunable hydrophilicity of a guest molecule on the solution behavior of mixed micelles of the guest and C 12 E 5 . Accordingly, the present work establishes a phase diagram of Blue-C 12 E 5 micelles and analyzes their morphology including the spatial distribution of Blue in the micelles as a function of the hydrophilicity of Blue. Small angle neutron scattering reveals the size and shape of the micelles, and detailed contrast matching of the C 12 E 5 supported by 1 H NMR with NOESY provided insight into the localization of Blue within the micelles as its hydrophilicity changes.

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The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry

Cited by 4 publications

References 29 publications

Exciton Coupling Effects in Polymeric cis-Indolenine Squaraine Dyes

Exciton Coupling Effects in Polymeric cis-Indolenine Squaraine Dyes

Isotope-Coded Maleimide Affinity Tags for Proteomics Applications

Impact of Additive Hydrophilicity on Mixed Dye-Nonionic Surfactant Micelles: Micelle Morphology and Dye Localization

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