A rational design of molecular materials

Fowler, Frank W.; Lauher, Joseph W.

doi:10.1002/1099-1395(200012)13:12<850::aid-poc316>3.0.co;2-l

Cited by 55 publications

(43 citation statements)

References 26 publications

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“…From the early beginnings of PDA formation, chemical transformations with diyne precursors have been advanced through the ability to control the reactions and gain a better understanding of the reaction mechanism. [82,88] Most recently, great success has come through using supramolecular hostguest strategies to control structural parameters that direct single-crystal-to-single-crystal polymerization reactions of diacetylenes. [80] Additionally, these controlled polymerizations can often be achieved under mild conditions, which increase functional group tolerance and facilitate post-polymerization synthetic steps.…”

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confidence: 99%

Carbon‐rich nanostructures: the conversion of acetylenes into materials

Chernick

Tykwinski

2013

J of Physical Organic Chem

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The inherent thermodynamic instability of the carbon-carbon triple bond offers a unique starting point for the formation of carbon-rich nanomaterials, which are of increasing importance for use in materials science and technology. Whereas significant efforts have recently been devoted toward suppressing the well-known reactivity of sp-hybridized compounds in an effort to obtain the elusive carbon allotrope "carbyne," this mini-review will focus on the opposite idea; that is, we explore current research efforts that attempt to harness the reactivity of carboncarbon triple bonds in a controlled, templated manner that ultimately converts acetylenic precursors into ordered, carbon-based nanomaterials.

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confidence: 99%

Carbon‐rich nanostructures: the conversion of acetylenes into materials

Chernick

Tykwinski

2013

J of Physical Organic Chem

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“…Intermolecular contacts within the layer are recognized at C1 and C4 whose distances Cocrystal of 1 with 2,2'-(oxalylbis(azanediyl))diacetic acid has already been reported by Fowler and Lauher [12]. In the cocrystal, 1 has anti conformation in the ester group and make an ideal orientation for solid-state-polymerization of diacetylenes by means of complexation with the template molecule.…”

Section: Crystal Structure Of 1-3mentioning

confidence: 72%

“…According CSD, there are four examples for crystal structures of diacetylene compounds which have a nicotinate or isonicotinate group [9,12,13,18,19]. No crystals showed polymerization reactivity which had gauche conformation at their ester parts including the present crystals.…”

Section: -4 Crystal Structures Of Other Diacetylenes Carrying a Nicomentioning

confidence: 97%

“…Preparation of compound 1-3 was shown in Scheme 1. Hay coupling of prop-2-yn-1-yl nicotinate gave symmetric diacetylene 1 with 69 % yield [12].…”

Section: -1 Preparation Of Compound 1-3mentioning

confidence: 99%

“…">General ProcedureAll chemicals were purchased from Kanto Chemical Co. Ltd. or Tokyo Kasei Kogyo Co. Ltd. and were used without further purification. Compound 1 was prepared according to the literature [12]. 1 H and 13 C NMR spectra were recorded on a JEOL JNM−ECA−400 spectrometer in a deuterated solvent (chloroform−d) with tetramethylsilane as an internal standard.…”

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confidence: 99%

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Preparations, crystal structures and DFT calculation of diacetylene derivatives carrying nicotinic esters

Minami

Iwahashi

Okuno

2016

Journal of Molecular Structure

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IntroductionPolydiacetylenes (PDAs), which are classified into conjugated polymers [1,2], have attracted not only from their physical properties originating from one-dimensional -conjugated systems such as non-linear optics [3] or conductivity [4][5][6], but also from application to chemosensors [7]. PDAs are prepared by solid-state-polymerization of diacetylene monomers, where relative orientation of monomers is quite important for the polymerization [8] because molecular motions are restricted in their crystals. Many PDAs have a -(CH 2 ) n -side chain adjacent to the backbone in order to reduce lattice strain caused by the solid-state polymerization. However, gauche or pseudo gauche conformation of the side chain frequently prevents suitable molecular orientation for the polymerization. Examples of the polymerization in gauche conformer are limited to some diacetylenes [9]. Pyridines have a large variety of chemical modification such as oxidation, protonation or N-alkylation [10]. Pyridines can also work as ligands for metal complexes or hydrogen-bond acceptors in supramolecular complexes [11]. PDAs carrying pyridyl pendant groups promise to give novel functional materials. Few PDAs carrying a pyridyl unit, however, have been reported as a single component judged by their crystal packing structures. While Lauher et al. have proposed several crystal designs for arranging pyridine-containing diacetylene derivatives by utilizing template molecules [12,13].We report herein preparation and crystal structures of novel three pyridine-containing diacetylenes and discuss their molecular structures based on intermolecular interactions and DFT calculation. Experimental General ProcedureAll chemicals were purchased from Kanto Chemical Co. Ltd. or Tokyo Kasei Kogyo Co. Ltd. and were used without further purification. Compound 1 was prepared according to the literature [12]. 1 H and 13 C NMR spectra were recorded on a JEOL JNM−ECA−400 spectrometer in a deuterated solvent (chloroform−d) with tetramethylsilane as an internal standard. All 13 C NMR spectra were obtained with complete proton decoupling. IR spectra were recorded on a JASCO FT/IR−420 spectrometer by using a KBr pellet. Elemental analysis was performed on a J−SCEINCE LAB MICRO CORDER JM10. Crystallographical analysisX-ray crystallographic data of 1-3 were obtained by a RIGAKU Saturn 724+ CCD device using multi-layered mirror monochromatic Mo K radiation at 93 K. The structures were solved by a direct method (SHELXD) [14] and were refined by full−matrix least-squares method (SHELXL97) [15]. The positions of non−H atoms were obtained from difference Fourier maps and were refined anisotropically. The C−bound H atoms were obtained by calculation and were refined as riding on their parent C atoms. U iso (H) values of the H atoms were set at 1.2U eq (parent C atoms). The N−bound and O−bound H atoms were obtained from difference Fourier maps and were refined isotropically. DFT calculationsDFT calculations were performed on the GAMESS software [16,17] with B3LYP 6-31G (d...

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Diacetylene and Triacetylene Polymers

Fowler

2002

Encyclopedia of Polymer Science and Technology

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The polyacetylenes, polydiacetylenes, and polytriacetylenes are the only known families of linearly conjugated polymers. The polydiacetylenes and polytriacetylenes, the primary topic of this discussion, are distinguished from the polyacetylenes because they require preorganization of the monomer for a successful polymerization. These topochemically controlled polymerizations have the interesting property that they can lead to single crystals of conjugated polymers, a unique structural feature among all polymers. The conjugated backbones impart interesting optical and electrical properties to these polymers, making them possible candidates for the development of advanced materials.

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A rational design of molecular materials

Cited by 55 publications

References 26 publications

Carbon‐rich nanostructures: the conversion of acetylenes into materials

Carbon‐rich nanostructures: the conversion of acetylenes into materials

Preparations, crystal structures and DFT calculation of diacetylene derivatives carrying nicotinic esters

Diacetylene and Triacetylene Polymers

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