Efficient Synthesis of a 2-Decyl-tetradecyl Substituted 7-Bromophenothiazine-3-carbaldehyde Building Block for Functional Dyes
Burak Kürsat Börüsah, Thomas J. J. Müller
Organics · pp. 502–506 · Published 7 Dec 2022
10.3390/org3040033Abstract
(1) Polyfunctional molecules are versatile building blocks for efficient syntheses of novel phenothiazine-based materials with promising electronic properties. A prerequisite is a facile, high yielding access to these building blocks that bear solubilizing moieties and functional groups for orthogonal transformation. (2) Here, an efficient, improved two-step protocol for accessing a solubilizing 2-decyl-tetradecyl functionalized phenothiazine, i.e., an N-alkylated 7-bromophenothiazine-3-carbaldehyde, by Vilsmeier–Haack formylation and NBS (N-bromo succinimide) bromination is reported. (3) The sequence proceeds with higher yields and in shorter reaction times than the standard access employing bromination with elementary bromine. In addition, the work-up procedure essentially uses absorptive filtration on a plug of silica with the eluent.
References (29)
- 1 Meyer, T., Krug, R., and Müller, T.J.J. (2021). Three-Component Suzuki–Knoevenagel Synthesis of Merocyanine Libraries and Correlation Analyses of Their Oxidation Potentials and Optical Band Gaps. Molecules, 26. [DOI]
- 2 Meyer, 2012, Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells [DOI]
- 3 Meyer, 2020, Consecutive Three-Component Synthesis of Donor-Substituted Merocyanines by a One-Pot Suzuki-Knoevenagel Condensation Sequence [DOI]
- 4 Hua, 2013, Significant Improvement of Dye-Sensitized Solar Cell Performance Using Simple Phenothiazine-Based Dyes [DOI]
- 5 Hauck, 2011, Synthesis, Electronic, and Electro-Optical Properties of Emissive Solvatochromic Phenothiazinyl Merocyanine Dyes [DOI]
- 6 Yang, 2012, Phenothiazine derivatives as organic sensitizers for highly efficient dye-sensitized solar cells [DOI]
- 7 Chen, 2012, Metal-free organic dyes derived from triphenylethylene for dye-sensitized solar cells: Tuning of the performance by phenothiazine and carbazole [DOI]
- 8 Iqbal, 2013, Impact of hydroxy and octyloxy substituents of phenothiazine based dyes on the photovoltaic performance [DOI]
- 9 Wang, 2014, Influence of the terminal electron donor in D–D–π–A phenothiazine dyes for dye-sensitized solar cells [DOI]
- 10 Dai, 2015, Synthesis and photovoltaic performance of asymmetric di-anchoring organic dyes [DOI]
- 11 Eiamprasert, 2018, Additional donor bridge as a design approach for multi-anchoring dyes for highly efficient dye-sensitized solar cells [DOI]
- 12 Jiao, 2018, Effects of meta or para connected organic dyes for dye-sensitized solar cell [DOI]
- 13 Revoju, 2018, Asymmetric triphenylamine–phenothiazine based small molecules with varying terminal acceptors for solution processed bulk-heterojunction organic solar cells [DOI]
- 14 Sachdeva, 2019, Logic gate based novel phenothiazine-pyridylhydrazones: Halochromism in solid and solution state [DOI]
- 15 Sachdeva, 2020, Fluorescent dyes for moisture detection in organic solvents: Push-pull based phenothiazine aldehydes with large Stokes shifts [DOI]
- 16 Chen, 2021, Phenothiazine and semi-cyanine based colorimetric and fluorescent probes for detection of sulfites in solutions and in living cells [DOI]
- 17 Zeitler, 2000, Synthesis of Functionalized Ethynylphenothiazine Fluorophores [DOI]
- 18 Wu, 2011, Synthesis of Ethynylated Phenothiazine Based Fluorescent Boronic Acid Probes [DOI]
- 19 Nagarajan, 2017, Novel ethynyl-pyrene substituted phenothiazine based metal free organic dyes in DSSC with 12% conversion efficiency [DOI]
- 20 Han, 2019, Synthesis and electrochemical, linear and third-order nonlinear optical properties of ferrocene-based D-π-A dyes as novel photoredox catalysts in photopolymerization under visible LED irradiations [DOI]
- 21 Slodek, 2019, Phenothiazine derivatives—Synthesis, characterization, and theoretical studies with an emphasis on the solvatochromic properties [DOI]
- 22 Slodek, 2021, “Small in size but mighty in force”—The first principle study of the impact of A/D units in A/D-phenyl-p-phenothiazine-p-dicyanovinyl systems on photophysical and optoelectronic properties [DOI]
- 23 Franz, 2009, First synthesis and electronic properties of diphenothiazine dumbbells bridged by heterocycles [DOI]
- 24 Stalindurai, 2017, Experimental and theoretical studies on new 7-(3,6-di-tert-butyl-9H-carbazol-9-yl)-10-alkyl-10H-phenothiazine-3-carbaldehydes [DOI]
- 25 Stalindurai, 2017, Fused heterocycles possessing novel metal-free organic dyes for dye-sensitized solar cells [DOI]
- 26 Stalindurai, 2017, Azafluorene Ornamented Thiazine Based Novel Fused Heterocyclic Organic Dyes for Competent Molecular Photovoltaics [DOI]
- 27 Arai, 2021, Chemical stimulus-responsive tricyanopyrroline-based ICT chromophore as a potential environment-sensitive probe [DOI]
- 28 Cao, 2014, Aggregation-induced and crystallization-enhanced emissions with time-dependence of a new Schiff-base family based on benzimidazole [DOI]
- 29 Mondal, 2018, Cage Encapsulated Gold Nanoparticles as Heterogeneous Photocatalyst for Facile and Selective Reduction of Nitroarenes to Azo Compounds [DOI]
Cited by 6
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