Synthesis and properties of a trapezoid shaped macrocycle with different [n]yne units

Desroches, Maude; Morin, Jean‐François

doi:10.1039/c7ra01721a

Cited by 4 publications

(5 citation statements)

References 21 publications

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“…Poly(Styrene-co-7-butoxybenzocyclobutene) (PSBBB) was prepared as demonstrated in Scheme 1, starting with the iodination of 4-bromophenol, which was synthesized using N-iodosuccinimide to generate 1 in 71% yield. 36 Phenol protection of 1 with HDMS to afford 2 was achieved quantitatively. N-BuLi addition to compound 2 at −78 °C provided compound 3 via an intramolecular rearrangement in 92% yield.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Low-Temperature Cross-Linking Benzocyclobutene Based Polymer Dielectric for Organic Thin Film Transistors on Plastic Substrates

et al. 2019

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The synthesis of a new benzocyclobutene based polymer, PSBBB, designed as a dielectric material for use in organic thin film transistors was reported. Compared to conventional benzocyclobutene-based materials, the introduction of a butoxide substituent at the 7-position of the benzocyclobutene pendant unit on the polymer allowed PSBBB to be cross-linked at temperatures of 120 °C, thus rendering it compatible with the processing requirements of flexible plastic substrates. The cross-linking behavior of PSBBB was investigated by Fourier transform infrared spectroscopy and differential scanning calorimetry, demonstrating cross-linking of the polymer after curing at 120 °C. Bottom-gate bottom-contact organic thin film transistors were fabricated using PSBBB as dielectric, affording a performance comparable to that of other dielectric polymeric materials.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…The synthesis of this molecule was achieved following the literature procedure. 36 The characterization data are in agreement with the published data.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Low-Temperature Cross-Linking Benzocyclobutene Based Polymer Dielectric for Organic Thin Film Transistors on Plastic Substrates

et al. 2019

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“…Typical macrocyclization reaction conditions require low concentration (i.e., high dilution) − or slow delivery of reactants (i.e., pseudo-dilution) ,− under inert conditions to suppress the formation of undesired oligomeric/linear byproducts. In our case, however, simple addition of L (ca.…”

Section: Resultsmentioning

confidence: 99%

From Foldable Open Chains to Shape-Persistent Macrocycles: Synthesis, Impact on 2D Ordering, and Stimulated Self-Assembly

et al. 2018

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Small molecule self-assembly at surfaces offers an efficient route to highly ordered organic films that can be programmed for a variety of chemical and electronic applications. The success of these materials depends on the ability to program intermolecular interactions to guide precise structural ordering. Toward this objective, we have designed and synthesized a series of bis(triazolo)benzene-based π-conjugated molecules. Our synthesis exploits a last-stage C-C cross-coupling reaction to close up zigzag-shaped linear precursors to cyclized products, so that direct side-by-side comparisons can be made for their structure-dependent self-assembly behavior at surfaces and response to external stimuli. Indeed, scanning tunneling microscopy (STM) analysis revealed distinct differences as the conformational flexibility of the molecular backbone and the chemical structure of the peripheral groups are varied. Specifically, alkyl chains adsorb and form interdigitated structures, whereas oligo ethylene glycol (OEG) chains remain desorbed and thus shift self-assembly to more densely packed π-conjugated cores. While the macrocycles self-assemble immediately and spontaneously, their linear precursors exhibit slower self-assembly kinetics, which could be attributed to the difference in the degree of conformational freedom. We also found that perturbation by the STM tip and the addition of cosolutes profoundly impacted the kinetics of self-assembly and surface patterning. This highly unusual behavior highlights the importance of noncovalent interactions that are inherently weak in solution but can be made strong for symmetric and conformationally restricted molecules confined within 2D surfaces.

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“…Macrocycle 110 with both ortho-a nd meta-phenyleneethynylene moieties was synthesized,w here the bond angles at all alkyne moieties are strain free (ff sp = 172-1798). [188] Tobe and co-workersa pplied the photoinduced elimination of indane to the synthesis of macrobicycles 111a (C 60 H 6 ), 111b (C 60 Cl 6 ), 112a (C 78 H 18 ), and 112b (C 78 H 12 Cl 6 ). [189][190][191] Interestingly,t he ion peak of C 60 H 6 À together with that of the fullerenea nion (C 60 À ) was detected during photoirradiation to 111,implying the possibility of fullerene synthesis from am acrobicycle.…”

Section: Reviewmentioning

confidence: 96%

“…By introducing donor/acceptor substituents on corner benzene rings in 108 and 109 , the fluorescence wavelength could be fine‐tuned. Macrocycle 110 with both ortho ‐ and meta ‐phenyleneethynylene moieties was synthesized, where the bond angles at all alkyne moieties are strain free (∠ sp =172–179°) . Tobe and co‐workers applied the photoinduced elimination of indane to the synthesis of macrobicycles 111 a (C 60 H 6 ), 111 b (C 60 Cl 6 ), 112 a (C 78 H 18 ), and 112 b (C 78 H 12 Cl 6 ) .…”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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Synthesis and properties of a trapezoid shaped macrocycle with different [n]yne units

Cited by 4 publications

References 21 publications

Low-Temperature Cross-Linking Benzocyclobutene Based Polymer Dielectric for Organic Thin Film Transistors on Plastic Substrates

Low-Temperature Cross-Linking Benzocyclobutene Based Polymer Dielectric for Organic Thin Film Transistors on Plastic Substrates

From Foldable Open Chains to Shape-Persistent Macrocycles: Synthesis, Impact on 2D Ordering, and Stimulated Self-Assembly

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

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