Dithienothiazine dimers, trimers and polymers – novel electron-rich donors with red-shifted luminescence

Nau, Jennifer; Schneeweis, Arno P. W.; Müller, Thomas J. J.

doi:10.1039/c9qm00591a

Cited by 7 publications

(35 citation statements)

References 37 publications

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Section: Concatenating Formylation With the Wittig Reaction Was Inspimentioning

confidence: 96%

“…Scheme 4. Diversity-oriented synthesis of syn-syn dithieno [1,4]thiazines 2a via inter-intra-molecular Buchwald-Hartwig coupling; a: Dielectric heating at 160 °C [35][36][37]. In the case of syn-syn isomers 2a the rather time-consuming synthesis according to Grol (Scheme 2) was cut short by an alternative strategy for generating the 1,4-thiazine ring.…”

Section: Syntheses Of Dithieno[14]thiazines By Cyclizing Buchwald-hamentioning

confidence: 99%

“…Important dithieno [1,4]thiazine building blocks 5, for example, aldehydes, iodides, or alcohols, are accessible with mostly good yields using dimethylformamide (DMF), iodine, or acetone as electrophiles, respectively [36,37].…”

Section: 6-functionalization Of Dithieno[14]thiazines: Expanding Tmentioning

confidence: 99%

“…For the synthesis of dimers 7b, another onepot sequence, namely a borylation-Suzuki coupling sequence, was developed circumventing the isolation of borylated intermediates (Scheme 14B). In contrast to the monomers 2a-f, these oligomers fluoresce redshifted and more intensively [37]. In addition, borylation of lithiated dithieno [1,4]thiazines can be carried out with trimethylborate as an electrophile, whereby pinacol-boronic acid esters, versatile substrates for Suzuki couplings, were obtained after subsequent esterification (Scheme 13) [37].…”

Section: Concatenating Formylation With the Wittig Reaction Was Inspimentioning

confidence: 99%

“…In contrast to the monomers 2a-f, these oligomers fluoresce redshifted and more intensively [37]. In addition, borylation of lithiated dithieno [1,4]thiazines can be carried out with trimethylborate as an electrophile, whereby pinacol-boronic acid esters, versatile substrates for Suzuki couplings, were obtained after subsequent esterification (Scheme 13) [37]. Scheme 12.…”

Section: Concatenating Formylation With the Wittig Reaction Was Inspimentioning

confidence: 99%

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Dithieno[1,4]thiazines and Bis[1]benzothieno[1,4]thiazines—Organometallic Synthesis and Functionalization of Electron Density Enriched Congeners of Phenothiazine

May

Müller

2020

Molecules

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This mini-review summarizes the syntheses and functionalizations of dithieno[1,4]thiazines and bis[1]benzothieno[1,4]thiazines, both electron density-enriched congeners of phenothiazines with remarkable electronic properties. Diversity-oriented, straightforward, and efficient syntheses, including versatile one-pot processes, have been developed for the anellated 1,4-thiazines as well as various functionalization for the expansion of the π-systems. Thereby, syntheses of different regioisomers depending on the (benzo)thieno-thiazine anellation are discussed, which exert a deep impact on the electronic properties. The tunable photophysical and electrochemical properties of dithieno[1,4]thiazines and bis[1]benzothieno[1,4]thiazines outscore phenothiazines on many points and promise an enormous potential in molecular electronics and applications beyond.

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Section: Concatenating Formylation With the Wittig Reaction Was Inspimentioning

confidence: 96%

Section: Syntheses Of Dithieno[14]thiazines By Cyclizing Buchwald-hamentioning

confidence: 99%

Section: 6-functionalization Of Dithieno[14]thiazines: Expanding Tmentioning

confidence: 99%

Section: Concatenating Formylation With the Wittig Reaction Was Inspimentioning

confidence: 99%

Section: Concatenating Formylation With the Wittig Reaction Was Inspimentioning

confidence: 99%

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Dithieno[1,4]thiazines and Bis[1]benzothieno[1,4]thiazines—Organometallic Synthesis and Functionalization of Electron Density Enriched Congeners of Phenothiazine

May

Müller

2020

Molecules

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Bis[1]benzothieno[1,4]thiaborins as a Platform for BODIPY Singlet Oxygen Photosensitizers

Marek

Urbanowicz

Wrochna

et al. 2023

Chemistry A European J

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A synthetic approach to two regioisomeric πelectron extended [1,4]thiaborins annulated with two benzothiophene units has been developed. The central thiaborin rings of the boracycles obtained exhibit different electronic properties; this is reflected in their different aromatic characters, boron Lewis acidity and UV-vis spectroscopic behavior. Thiaborins were converted to boron dipyrromethene (BODIPY) complexes. Their emission spectra exhibit two distinct bands resulting from 1 LE and 1 CT transitions. Strong near-infrared phosphorescence in Zeonex thin films at 77 K indicates efficient intersystem crossing and the formation of triplet states. Separation of HOMO and LUMO orbitals between boracyclic and BODIPY moieties facilitates electron transfer to a 1 CT state followed by a transition to the 3 LE triplet state located on the ligand. These unique properties of spiro thiaborin-BODIPY complexes were explored for their application as singlet-oxygen photosensitizers. They show excellent photocatalytic performance with singlet oxygen quantum yields reaching 77 % and full conversion of the model organic substrate achieved after 1.5 h with only 0.05 % mol catalyst load.

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Synthesis and Electronic Properties of Conjugated syn,syn‐Dithienothiazine Donor‐Acceptor‐Donor Dumbbells

et al. 2022

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A series of conjugated syn,syn‐dithienothiazine donor‐acceptor‐donor dumbbells is readily synthesized by Suzuki coupling or a one‐pot α‐lithiation‐zincation‐Negishi coupling sequence in moderate to good yield. The title compounds are all electron‐rich reversible oxidizable redox systems with a relatively narrow range of oxidation potentials according to cyclic voltammetry. UV/Vis and fluorescence spectroscopy however show a significant effect of the electronic nature of the conjugated bridging system on absorption and emission characteristics. Furthermore, a highly polar excited state can be corroborated by Lippert‐Mataga analysis of the emission solvatochromicity as well as by TD‐DFT calculation of absorption and emission maxima, which classify these dumbbell systems as redox active, luminescent low band gap chromophores with experimentally determined optical band gaps between 2.20 and 2.50 eV.

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Dithienothiazine dimers, trimers and polymers – novel electron-rich donors with red-shifted luminescence

Abstract: Dithienothiazine oligomers and polymers display significant red shifted luminescence and low oxidation potentials.

Cited by 7 publications

References 37 publications

Dithieno[1,4]thiazines and Bis[1]benzothieno[1,4]thiazines—Organometallic Synthesis and Functionalization of Electron Density Enriched Congeners of Phenothiazine

Dithieno[1,4]thiazines and Bis[1]benzothieno[1,4]thiazines—Organometallic Synthesis and Functionalization of Electron Density Enriched Congeners of Phenothiazine

Bis[1]benzothieno[1,4]thiaborins as a Platform for BODIPY Singlet Oxygen Photosensitizers

Synthesis and Electronic Properties of Conjugated syn,syn‐Dithienothiazine Donor‐Acceptor‐Donor Dumbbells

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