Linear π‐conjugated polymers containing 2,4,6‐tris(thiophen‐2‐yl)‐1,3,5‐triazine unit: Synthesis and optical properties

Zou, Li; Fu, Yang; Yan, Xuehai; Chen, Xingguo; Qin, Jingui

doi:10.1002/pola.22418

Cited by 24 publications

(28 citation statements)

References 98 publications

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“…The measurements were conducted in a 0.1 M TBAPF 6 acetonitrile solution at room temperature under argon with a scan rate of 100 mV Á s À1 , and calibrated against ferrocene (Fc) with an ionization potential (IP) value of 4.8 eV below the vacuum level. [13] Figure 3 depicts the oxidation and reduction processes of the polymers. All the polymers show well-defined quasi-reversible reduction and oxidation processes.…”

Section: Resultsmentioning

confidence: 99%

Highly Fluorescent Conjugated Copolymers Containing Dithieno[3,2‐b:2′,3′‐d]pyrrole

Zhang

Bao³

et al. 2008

Macromol. Rapid Commun.

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Three copolymers that incorporate dithieno[3,2‐b:2′,3′‐d]pyrrole with fluorene, carbazole, or pyridine have been prepared by Suzuki reaction and characterized by NMR spectroscopy and GPC. A new homopolymer of dithieno[3,2‐b:2′,3′‐d]pyrrole was also synthesized for the comparison of their structure–property relationships. Their thermal, optical, and electrochemical properties have been investigated. All the polymers exhibit good thermal stability with decomposition temperatures around 400 °C. The fluorescence quantum efficiencies of all these polymers in solution are in the range of 33.5–55.5%. The copolymers also show high film fluorescence quantum efficiencies of about 20% while the fluorescence of the homopolymer film is almost quenched.magnified image

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Section: Resultsmentioning

confidence: 99%

Highly Fluorescent Conjugated Copolymers Containing Dithieno[3,2‐b:2′,3′‐d]pyrrole

Zhang

Bao³

et al. 2008

Macromol. Rapid Commun.

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“…reported the synthesis of star‐shaped molecules 127 and 129 , which comprised an electron‐accepting unit, such as 1,3,5‐triazine, as a central core and thiophen‐2‐yl spacer units connected to aromatic side arms . Their synthetic sequence began with the trimerization of thiophene‐2‐carbonitrile ( 123 ) in the presence of CF 3 SO 3 H to deliver 2,4,6‐tris(thiophen‐2‐yl)triazine ( 124 ) . Subsequent treatment of the trimerized product ( 124 ) with NBS in DMF gave the key precursor, 1,3,5‐triazine derivative 125 , along with the corresponding dibromo derivative.…”

Section: Carbon−carbon Bond Formationmentioning

confidence: 99%

“…[11] We also reported the synthesis of star-shaped AAA derivative 25 from the SM cross-coupling of triiodobenzene ( 12) with AAA-containing boronic acid 23 (Scheme 8). [10] Okumoto and Shirota synthesized new star-shaped molecules, such as 1,3,5-tris(4-fluorobiphenyl-4'-yl)benzene (29)a nd 1,3,5-tris[4- (9,9-dimethylfluoren-2-yl)phenyl]benzene (30), as hole-blocking amorphous materials. [12] Furthermore, they also showedt he applicabilityo ft hese compounds in blue-violetfluorescent and green-phosphorescent organic electroluminescent devices.…”

Section: Suzuki-miyaura Cross-coupling Reactionsmentioning

confidence: 99%

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Kotha

Meshram

Panguluri

et al. 2019

Chemistry An Asian Journal

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Herein, we summarize the synthetic approaches that have been developed for the synthesis of star‐shaped molecules. Typically, to design such highly functionalized molecules, simple building blocks are first assembled through trimerization reactions, starting from commercially available starting materials. Then, these building blocks are synthetically manipulated to generate extended star‐shaped molecules. We also discuss the syntheses of star‐shaped molecules that contain 2,4,6‐trisubstituted 1,3,5‐triazine or 1,3,5‐trisubstituted benzene rings as a central core and diverse substituted styrene, phenyl, and fluorene derivatives at their periphery, which endows these molecules with extended conjugation. A variety of metal‐catalyzed reactions, such as Suzuki, Buchwald–Hartwig, Sonogashira, Heck, and Negishi cross‐coupling reactions, as well as metathesis, have been employed to functionalize a range of star‐shaped molecules. The methods described herein will be helpful for designing a wide range of intricate compounds that are highly valuable in the fields of supramolecular chemistry and materials science. Owing to space limitations, we will not cover all of the publications on this topic. Instead, we will focus on examples that were reported by our research group and other relevant recent literature. Apart from the trimerization sequence, this Minireview has been structured based on the key reactions that were used to prepare the star‐shaped molecules and other higher analogues. Finally, some examples that do not fit into this classification are discussed.

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“…14 The alkynes were prepared through Pd(0)-catalyzed Sonogashira coupling from the corresponding bromo-or iodine-aromatic compounds and ethynyl-trimethylsilane. 15 The CuAAC reaction was carried out in a typical procedure described in reference, 3 in which in-situ generated Cu(I) cation had been employed as catalyst and excess azides was applied to ensure the full conversion of alkyne component. In each reaction, 2% molar ratio of the catalyst and 10% molar ratio of the reducing reagent in aqueous solution (fresh-generated sodium ascorbate) had been added.…”

Section: Synthesismentioning

confidence: 99%

Synthesis of Click‐Chelator via Cu(I)‐Catalyzed Alkyne‐Azide Cycloaddition

Liu

et al. 2010

Chin. J. Chem.

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The click-ligands based on 1,2,3-triazole and pyridine unit has been synthesized via Cu(I)-catalyzed alkyneazide cycloaddition from corresponding organic azides and terminal alkynes. The ligand structure was characterized by NMR, IR and elemental analysis as well as single crystal diffractions. The single crystal structure of the complexes from two different ligands coordinating to Cu(II) and Co(II) ions indicated that the N(2) atom in 1,2,3-triazole unit can act as an efficient donor to metals through the rational molecular design.

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Linear π‐conjugated polymers containing 2,4,6‐tris(thiophen‐2‐yl)‐1,3,5‐triazine unit: Synthesis and optical properties

Cited by 24 publications

References 98 publications

Highly Fluorescent Conjugated Copolymers Containing Dithieno[3,2‐b:2′,3′‐d]pyrrole

Highly Fluorescent Conjugated Copolymers Containing Dithieno[3,2‐b:2′,3′‐d]pyrrole

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Synthesis of Click‐Chelator via Cu(I)‐Catalyzed Alkyne‐Azide Cycloaddition

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