Synthesis and properties of α-oligothiophenes carrying three cofacially oriented thiophene rings through peri positions of naphthalenes

Kuroda, Masami; Nakayama, Juzo; Hoshino, Minoru; Furusho, Noboru; Ohba, Shigeru

doi:10.1016/s0040-4039(00)76712-8

Cited by 19 publications

(6 citation statements)

References 13 publications

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“…The above shown model compound 4 shows an absorption peak at 449 nm in CHCl 3 (no. 9), which is shifted to a longer wavelength from those of an analogous trimeric compounds, 2,5-bis(2-thienyl)pyridine (340 nm), and related naphthalene-thiophene derivatives …”

Section: Resultsmentioning

confidence: 99%

Syntheses of New Alternating CT-Type Copolymers of Thiophene and Pyrido[3,4-b]pyrazine Units: Their Optical and Electrochemical Properties in Comparison with Similar CT Copolymers of Thiophene with Pyridine and Quinoxaline

1999

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Four kinds of new π-conjugated copolymers of electron-donating thiophene with highly electron-withdrawing pyrido[3,4-b]pyrazine derivatives have been prepared by using the Stille reaction and electrochemical oxidative polymerization in high yields, and their optical and electrochemical properties have been compared with those of previously reported CT-type π-conjugated polymers. Chemically prepared polymers show an [η] value of about 0.3 dL g-1. The π−π* absorption bands (λmax = ca. 633 nm) of the copolymers are observed at a longer wavelength by about 30 nm than those of similar CT-type copolymers of thiophene with pyridine and quinoxaline. These UV−vis data are considered to reflect a stronger CT interaction between thiophene and pyrido[3,4-b]pyrazine, which has a higher electron-withdrawing ability than pyridine and quinoxaline. The copolymers are electrochemically active in both oxidation and reduction regions. In the reduction (n-doping) region, the copolymers show normal three couples of n-doping and n-undoping between −1.55 and −2.25 V vs Ag/Ag+. On the other hand, they receive oxidation (p-doping) at E pa of 0.9 V vs Ag/Ag+. The electrochemical p- and n-doping of the film of the copolymers is accompanied by changes in its UV−vis spectra (electrochromism), and new absorption bands emerge in the range 900−1500 nm by the p- and n-doping. The X-ray diffraction pattern of the copolymer having a long alkyl side chain suggests self-assembling of the polymer assisted by side chain crystallization.

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Section: Resultsmentioning

confidence: 99%

Syntheses of New Alternating CT-Type Copolymers of Thiophene and Pyrido[3,4-b]pyrazine Units: Their Optical and Electrochemical Properties in Comparison with Similar CT Copolymers of Thiophene with Pyridine and Quinoxaline

1999

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“…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. Nakayama and co-workers [60][61][62] and Iyoda and co-workers 63,64 have reported the synthesis of cofacially oriented naphthalene-based oligothiophenes, in which two or three bithiophenes were layered. In addition, Iyoda and co-workers have synthesized 2,2¢-bithiophenophanes.…”

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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“…More efficient methods for the synthesis of compound 54 turned out to be the Negishi coupling between diiodide 7 and (thienyl‐2)zinc chloride in the presence of Pd(PPh 3 ) 4 (59 % yield), [101] as well as the Suzuki arylation of dibromide 23 with thiophene‐2‐boronic acid (73 % yield) [50] . Compound 54 was used to synthesize oligothiophenes 168 ‐ 172 [98–101] . Crystal structures and theoretical calculations show the presence of through conjugation along bonds and through space in such oligomers, which allows the use of two transport channels and is useful for improving their redox activity and stability.…”

Section: Synthesis and Applications Of 18‐dihetarylnaphthalenesmentioning

confidence: 99%

“…[50] Compound 54 was used to synthesize oligothiophenes 168-172. [98][99][100][101] Crystal structures and theoretical calculations show the presence of through conjugation along bonds and through space in such oligomers, which allows the use of two transport channels and is useful for improving their redox activity and stability. Electropolymerization of 1,8-dithienylnaphthalene was carried out.…”

Section: Synthesis and Applications Of 18-dihetarylnaphthalenesmentioning

confidence: 99%

1,8‐Diarylnaphthalenes: Synthesis, Properties, and Applications

Gulevskaya

Ермоленко

2022

Eur J Org Chem

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Diarylnaphthalenes are a fascinating example of strained organic molecules that have found many practical applications due to unusual parallel face-to-face arrangement of two periaryl rings in close proximity almost perpendicular to the central naphthalene backbone. 1,8-Diarylnaphthalenes show notable potential as photoluminescent and chiral sensors, stereodynamic switches, nonlinear optic chromophores, blue-transparent frequency doublers, materials for creating high-performance blue and green OLEDs, chiral ligands and so on. Molecules of this type have also been used as convenient models for studying π-π, dipole-π and cation-π interactions. 1,8-Diarylnaphthalenes are also interesting as objects to study atropisomeric transformations: if the peri-aryl rings have ortho-or metasubstituents, then the anti-conformer becomes C 2 -symmetrical (hence chiral), and the syn-isomer upon symmetrical substitution is achiral. In this review, data on synthetic methods, applications, atropisomerism and structural characteristics of 1,8-diaryl-and 1,8-dihetarylnaphthalenes are summarized.

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Synthesis and properties of α-oligothiophenes carrying three cofacially oriented thiophene rings through peri positions of naphthalenes

Cited by 19 publications

References 13 publications

Syntheses of New Alternating CT-Type Copolymers of Thiophene and Pyrido[3,4-b]pyrazine Units: Their Optical and Electrochemical Properties in Comparison with Similar CT Copolymers of Thiophene with Pyridine and Quinoxaline

Syntheses of New Alternating CT-Type Copolymers of Thiophene and Pyrido[3,4-b]pyrazine Units: Their Optical and Electrochemical Properties in Comparison with Similar CT Copolymers of Thiophene with Pyridine and Quinoxaline

Naphthalene-based oligothiophene-stacked polymers

1,8‐Diarylnaphthalenes: Synthesis, Properties, and Applications

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