[2.2]Paracyclophane-Layered Polymers End-Capped with Fluorescence Quenchers

Morisaki, Yasuhiro; Murakami, Takuya; Sawamura, T.; Chujo, Yoshiki

doi:10.1021/ma9000644

Cited by 47 publications

(24 citation statements)

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“…[26][27][28][29][30] We have recently reported the synthesis of polymers with layered aromatic rings using a xanthene scaffold as a hairpin-shaped linker; these polymers exhibit intramolecular π-stacked structures with multiple aromatic rings stacked along a single polymer chain. [31][32][33][34][35][36] They can be regarded as the assembly of several small π-conjugated units. However, owing to the small size of the π-conjugated moieties and to the bulkiness of the xanthene scaffold, their intermolecular interactions were relatively weak.…”

Section: Introductionmentioning

confidence: 99%

π-Conjugated polymer-layered structures: synthesis and self-assembly

Tsuji

Morisaki

Chujo

2016

Polym J

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π-Conjugated polymers capped with a boronic acid end-functional group were synthesized by chain-growth Suzuki-Miyaura polycondensation. The obtained polymers were reacted with a π-stacked-polymer scaffold, developed in our previous work. Despite their bulkiness, the conjugated polymers were efficiently introduced into the polymer scaffold. The spectroscopic and optical characterization of the obtained graft polymers in the solid state revealed that the original π-conjugated polymers were stacked in a single polymer chain. Although excluded volume effects prevented significant intermolecular interactions between the polyfluorenes, the introduced polythiophenes formed intermolecular π-stacked structures. Direct observations of the obtained graft polymers showed that the graft polymers self-assembled into the spherical or fiber structures depending on the introduced polymers, whereas no ordered structures were formed by the same polymers before the polymer reaction.

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Section: Introductionmentioning

confidence: 99%

π-Conjugated polymer-layered structures: synthesis and self-assembly

Tsuji

Morisaki

Chujo

2016

Polym J

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“…55 We have recently reported the synthesis of aromatic-ring-layered polymers using xanthene compounds as scaffolds. [40][41][42][43][44][45][46][47] [2.2] Paracyclophane-layered polymers, which mimic multilayered cyclophanes, 56-59 exhibited fluorescence resonance energy transfer from the layered paracyclophanes to the end-capping groups. The use of xanthene as a scaffold enabled us to introduce various aromatic compounds, such as phenylenes, 44 carbazoles, 45 thiophenes 46 and anthracene, 47 into the polymers, with the distance between the layered aromatic units being B4.5 Å .…”

Section: Introductionmentioning

confidence: 99%

“…Poly(dibenzofulvene)s, 4-11 7,7-diarylnorbornane-containing conjugated polymers, 12,13 cyclophanecontaining polymers and face-to-face ferrocene polymers [36][37][38] have been synthesized, and their optical and electrochemical properties have been studied in detail. Polymers with layered aromatic rings and p-electron systems have also been investigated; [39][40][41][42][43][44][45][46][47][48][49][50][51][52][53] for example, Chen et al 53 recently reported the synthesis and formation of a twodimensional assembly of polymeric ladder phanes containing face-toface p-electron systems. These polymers have potential applications in optoelectronic devices and single-molecular devices such as singlemolecular wires.…”

Section: Introductionmentioning

confidence: 99%

Naphthalene-based oligothiophene-stacked polymers

Morisaki

Fernandes

Chujo

2010

Polym J

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We report the synthesis and properties of p-stacked polymers consisting of oligothiophene and naphthalene as the stacked p-system and the scaffold, respectively. The titled polymers were obtained by the Suzuki-Miyaura coupling reaction. Oligothiophene units were layered in proximity, B3.0 Å from each other. Contribution of the quinoidal structure of the oligothiophene units involving the naphthalene scaffolds in the excited state resulted in relatively high photoluminescence quantum efficiencies. The polymers have potential application to optoelectronic devices such as hole-transporting materials. Polymer Journal (2010) 42, 928-934; doi:10.1038/pj.2010.101; published online 27 October 2010Keywords: conjugated polymers; p-stacked polymers; oligothiophene; redox polymers; synthesis INTRODUCTIONCommon conjugated polymers generally consist of sp-and/or sp 2 -carbon frameworks, and p-electrons are delocalized throughout the polymer backbone. Such conjugated polymers have attracted considerable attention because of their good processability and their readily tunable electronic and optical properties. [1][2][3] Recently, a new type of conjugated polymer that exhibits through-space interactions of pelectron systems has been developed. Poly(dibenzofulvene)s, 4-11 7,7-diarylnorbornane-containing conjugated polymers, 12,13 cyclophanecontaining polymers and face-to-face ferrocene polymers [36][37][38] have been synthesized, and their optical and electrochemical properties have been studied in detail. Polymers with layered aromatic rings and p-electron systems have also been investigated; 39-53 for example, Chen et al. 53 recently reported the synthesis and formation of a twodimensional assembly of polymeric ladder phanes containing face-toface p-electron systems. These polymers have potential applications in optoelectronic devices and single-molecular devices such as singlemolecular wires.Cofacially aligned p-electron systems have an important role in biochemistry and material chemistry; DNA has face-to-face base pairs stacked in the double-stranded main chains, 54 and the performance of organic optoelectronic devices strongly depends on the arrangement of the p-electron systems. 55 We have recently reported the synthesis of aromatic-ring-layered polymers using xanthene compounds as scaffolds. [40][41][42][43][44][45][46][47] [2.2] Paracyclophane-layered polymers, which mimic multilayered cyclophanes, 56-59 exhibited fluorescence resonance energy transfer from the layered paracyclophanes to the end-capping groups. The use of xanthene as a scaffold enabled us to introduce various aromatic compounds, such as phenylenes, 44 carbazoles, 45 thiophenes 46 and anthracene, 47 into the polymers, with the distance between the layered aromatic units being B4.5 Å . Our next target is to construct layered and p-stacked aromatic systems in proximity, less than the sum of the van der Waals radius (3.40 Å ) of an sp 2 -carbon, in the polymer backbone.

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“…Moreover, these compounds have been incorporated into conjugated polymer backbones as conjugation systems, which can enhance the photoluminescence (PL), electroluminescence, and liquid crystallinity of the polymers. [32,33] It is, thus, worthwhile to design a xanthene-based aromatic diamine as a starting monomer for preparation of high-performance polyamides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel aliphatic–aromatic polyamide/Fe₃O₄ nanocomposites containing pendent 9H-xanthene groups

Moghanian

Mobinikhaledi

Monjezi

2014

Designed Monomers and Polymers

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New magnetic polyamide/Fe 3 O 4 nanocomposites containing pendent 9H-xanthene were prepared via solution intercalation technique from polyamide 9 and Fe 3 O 4 nanoparticle in a solution of N,N-dimethylacetamide. A new polyamide 9 as a source of polymeric matrix was synthesized by direct polycondensation reaction of 3,5-diamino-N-(4-(1,3,6,8-tetramethyl-9H-xanthen-9-yl)phenyl)benzamide (7) with adipic acid in a medium consisting of N-methyl-2-pyrrolidone, riphenyl phosphite, calcium chloride, and pyridine. The synthesized polyamide was characterized by Fourier transform infrared spectra, nuclear magnetic resonance, UV-vis, and photoluminescence spectroscopy. The structural and electronic properties of xanthene-based polyamide unit were studied by ab initio density functional theory method using the B 3 LYP/6-31G (d) level of theory. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LOMO) level energy, and band gap (ΔE = E LUMO − E HOMO ) of the polyamide unit were calculated. Fe 3 O 4 nanoparticles have been synthesized using a chemical co-precipitation route. Using a combination of dissolving the polymer and mixing Fe 3 O 4 nanoparticles, we have demonstrated the formation of nanocomposites with uniform nanoparticle dispersion. The morphology, crystalline phase, thermal stability, and magnetization properties of the resultant materials were characterized by means of transmission electron microscope, X-ray diffraction, thermal gravimetric analysis, and vibrating sample magnetometer. The results indicated that the as-prepared nanocomposites exhibited superparamagnetic properties and improvements in the thermal stability compared to neat polyamide.

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[2.2]Paracyclophane-Layered Polymers End-Capped with Fluorescence Quenchers

Cited by 47 publications

References 54 publications

π-Conjugated polymer-layered structures: synthesis and self-assembly

π-Conjugated polymer-layered structures: synthesis and self-assembly

Naphthalene-based oligothiophene-stacked polymers

Synthesis and characterization of novel aliphatic–aromatic polyamide/Fe₃O₄ nanocomposites containing pendent 9H-xanthene groups

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[2.2]Paracyclophane-Layered Polymers End-Capped with Fluorescence Quenchers

Cited by 47 publications

References 54 publications

π-Conjugated polymer-layered structures: synthesis and self-assembly

π-Conjugated polymer-layered structures: synthesis and self-assembly

Naphthalene-based oligothiophene-stacked polymers

Synthesis and characterization of novel aliphatic–aromatic polyamide/Fe3O4 nanocomposites containing pendent 9H-xanthene groups

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Product

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Synthesis and characterization of novel aliphatic–aromatic polyamide/Fe₃O₄ nanocomposites containing pendent 9H-xanthene groups