Short-step syntheses and complexation properties of Z,Z-tribenzodidehydro- and all-Z-tribenzo[12]annulenes

Sirinintasak, Siriwan; Kuwatani, Yoshiyuki; Hoshi, Shinichi; Isomura, Eigo; Nishinaga, Tohru; Iyoda, Masahiko

doi:10.1016/j.tetlet.2007.03.044

Cited by 17 publications

(9 citation statements)

References 17 publications

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“…[16] Asubstantial limitation of the initial synthesis of 21 by Iyoda et al is the low yield of the last step. To circumvent the shortcoming of this route,I yoda and coworkers developed anew method for the synthesis of 21, [17] in which tribenzohexadehydroannulene 23 was hydrogenated by Ti(O i Pr) 4 / i PrMgCl, thus providing direct access to 21 in higher yield. Thesynthesis of benzannulenes of various size was also accomplished (Scheme 8).…”

Section: Katsuma Matsui Was Born Inmentioning

confidence: 99%

Design and Synthesis of Carbon Nanotube Segments

et al. 2016

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Section: Katsuma Matsui Was Born Inmentioning

confidence: 99%

Design and Synthesis of Carbon Nanotube Segments

et al. 2016

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“…[21] Furthermore, the new synthetic route could be used to prepare higher benzoannulenes 12-14 ( Figure 3). [19, 22a] Interestingly, X-ray analysis of benzo [24]annulene 14 showed that it adopts C 3 conformation 14 a with three CH-p interactions, and the triangular arrangement of three benzene rings in 14 a (a: 4.70 ; b: 4.59 ; c:…”

Section: Annulenes and Dehydroannulenesmentioning

confidence: 99%

Conjugated Macrocycles: Concepts and Applications

2011

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One of the most important objectives in materials, chemical, and physical sciences is the creation of large conjugated macrocycles with well-defined shapes, since such molecules are not only theoretically and experimentally interesting but also have potential applications in nanotechnology. Fully unsaturated macrocycles are regarded as models for infinitely conjugated π systems with inner cavities, and exhibit unusual optical and magnetic behavior. Macrocycles have interior and exterior sites, and site-specific substitution at both or either site can afford attractive structures, such as 1D, 2D, and 3D supramolecular nanostructures. These nanostructures could be controlled through the use of π-extended large macrocycles by a bottom-up strategy. Numerous shape-persistent π-conjugated macrocycles have been synthesized, but only a few are on the nanoscale. This Review focuses on nanosized π-conjugated macrocycles (>1 nm diameter) and giant macrocycles (>2 nm diameter), and summarizes their syntheses and properties.

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“…[28] Moreover, 1 was recently synthesized by the reaction of hexadehydrotribenzo [12]annulene with a low-valent titanium reagent. [29] Although 1 has a larger peripheral π frame than DBCOT, 1 shows shorter UV absorption [λmax (cyclohexane) 219sh (log ϵ 4.50) and 267sh (3.23) nm] than DBCOT [λmax (cyclohexane) 241 (4.50) and 274 (3.46) nm]. The most remarkable property of 1 is inclusion of a metal cation such as Ag + or Cu + , and the three double bonds effectively coordinate to the metal cation in the central cavity.…”

Section: Cyclooctatetraene and All-z-tribenzo[12]annulenementioning

confidence: 99%

“…We further improved the synthesis of 1 starting from the dialdehyde, and it can now be prepared on a gram scale [28]. Moreover, 1 was recently synthesized by the reaction of hexadehydrotribenzo[12]annulene with a low‐valent titanium reagent [29]…”

Section: Introductionmentioning

confidence: 99%

Bent π‐Conjugated Systems Composed of Three‐Dimensional Benzoannulenes

Nishiuchi

Iyoda

2015

The Chemical Record

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This article describes bent π-conjugated systems composed of alternating o-phenylene and Z-vinylene units. all-Z-[n]Benzo[4n]annulenes are higher homologues of dibenzocyclooctatetraene (DBCOT) with a concave π system, and attempts were made to convert [20]- and [24]annulenes having partial belt structures of fullerenes and carbon nanotubes into [10]- and [12]phenacenes. A bent π-conjugated system composed of two DBCOT units showed dynamic syn-anti equilibrium in solution and behaved as dynamic molecular tweezers (DMTs). The syn isomers of the DMTs formed blue charge-transfer complexes with DDQ in solution, and this complexation and color change were applied to thermochromism. Furthermore, DMTs having two CN groups on each COT ring exhibited crystalline-state emission in the presence of solvent molecules, although almost no emission was observed in solution or the solid state. Based on this crystalline-state emission, a vapochromic system was established. The multifunctional properties of DMTs caused by the flexibility of the nonplanar π system are summarized.

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Short-step syntheses and complexation properties of Z,Z-tribenzodidehydro- and all-Z-tribenzo[12]annulenes

Cited by 17 publications

References 17 publications

Design and Synthesis of Carbon Nanotube Segments

Design and Synthesis of Carbon Nanotube Segments

Conjugated Macrocycles: Concepts and Applications

Bent π‐Conjugated Systems Composed of Three‐Dimensional Benzoannulenes

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