Synthesis and properties of novel C3-symmetrical 1,3,5-tris(dibenzoheterolyl)benzenes

Shimasaki, Toshiaki; Takiyama, Yuichiro; Nishihara, Yuki; Morimoto, Asami; Teramoto, Naozumi; Shibata, Mitsuhiro

doi:10.1016/j.tetlet.2014.11.080

Cited by 14 publications

(18 citation statements)

References 26 publications

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“…To realize the strategy shown in Figure 1, we begin our journey with the trimerization 12 of 2-acetyl-4-bromo thiophene ( 1 ) by using the known trimerization conditions. 13 However, we did not get the desired product 2 . Therefore, we changed the route to prepare the tri-bromo compound 2 .…”

Section: Resultsmentioning

confidence: 91%

Synthesis and Photophysical Properties of C₃-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

et al. 2017

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We report simple strategies to synthesize star-shaped molecules containing different heterocycles integrated with a number of variations. Here, cyclotrimerization, Vilsmeier–Haack reaction, Suzuki–Miyaura cross-coupling, and Van Leusen oxazole synthesis have been used as key steps to introduce diverse five-membered heterocycles such as furan, thiophene, and oxazole. More importantly, readily available starting materials such as thiophene, 2-formyl furan, and 2-acetyl furan were utilized. Also, the fluorescent behavior of these π-conjugated systems was studied. C 3 -Symmetric molecules containing furan moieties show a stronger fluorescence than thiophene-containing star-shaped compounds.

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Section: Resultsmentioning

confidence: 91%

Synthesis and Photophysical Properties of C₃-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

et al. 2017

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“…Shimasaki et al. reported the synthesis of 1,3,5‐tris(dibenzoheterolyl)benzenes 252 a – 252 c by employing an acid‐catalyzed cyclization reaction of acetyldibenzoheteroles 251 a – 251 c (Scheme ) . The photophysical and electrochemical properties of these compounds were also studied.…”

Section: Carbon−carbon Bond Formationmentioning

confidence: 99%

“…Shimasaki et al reported the synthesis of 1,3,5-tris(dibenzoheterolyl)benzenes 252 a-252 c by employing an acid-catalyzed cyclization reactiono fa cetyldibenzoheteroles 251 a-251 c (Scheme 79). [60] The photophysical and electrochemical properties of these compounds were also studied. The cyclization reactionw as performed by using ar ange of catalysts, such as SOCl 2 ,4 -dodecylbenzenesulfonic acid (DBSA), CF 3 SO 3 H, and SiCl 4 .A fter some experimentation,i tw as found that, for compound 251 a,t he use of DBSA in meta-xylene at 130 8Cf or 24 hg ave the corresponding cyclized star-shaped product (252 a)i nt he highest yield (66 %).…”

Section: Trimerization 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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“…Star-shaped molecules based on 1,3,5-triarylbenzenes have long been recognized as a family of amorphous glasses stable above room temperature. 1,2 The bioisosteric replacement of benzene by thiophene has extended the family of C 3 -symmetric compounds 3,4 and their applications in electroluminescent (EL) devices, 5 liquid crystalline materials 6 and as fluorescent probes. 7 In contrast to polymers used in similar applications, amorphous molecular materials are pure materials with well-defined molecular structures and definite molecular weights without any distribution.…”

Section: Introductionmentioning

confidence: 99%

Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds

Andicsovà‐Eckstein¹,

Végh²,

Krutošíková³

et al. 2018

Arkivoc

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The acid catalysed triple self-condensation of 1-thien-2-ylethanone (2-acetylthiophene) and five related compounds is presented. Tetrachlorosilane used as the Lewis acid produces dry hydrogen chloride which catalyzes the self-condensation process. Depending on the reaction conditions and the substitution of the carbonyl substrates, the reaction can proceed as a [2+2+2] cyclotrimerization towards C 3 -symmetric 1,3,5trisubstituted benzenes, or as the single-type aldol condensation leading to 1,3-disubstituted (E)-β-methylchalcones. This is important for the design of new aromatic/olefinic compounds beyond the model structures. Synthesis of 4'-fluoro-3,5-di-(2-thienyl)biphenyl through a mixed-type aldol reaction using erbium triflate is discussed. Mechanistic rationale is provided.

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Synthesis and properties of novel C3-symmetrical 1,3,5-tris(dibenzoheterolyl)benzenes

Cited by 14 publications

References 26 publications

Synthesis and Photophysical Properties of C₃-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

Synthesis and Photophysical Properties of C₃-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

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

Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds

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Synthesis and properties of novel C3-symmetrical 1,3,5-tris(dibenzoheterolyl)benzenes

Cited by 14 publications

References 26 publications

Synthesis and Photophysical Properties of C3-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

Synthesis and Photophysical Properties of C3-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

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

Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds

Contact Info

Product

Resources

About

Synthesis and Photophysical Properties of C₃-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole

Synthesis and Photophysical Properties of C₃-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole