Synthesis, structure, and both cathodic and anodic reversible redox reactions of benzochalcogenophenes containing ferrocene units

Ogawa, Satoshi; Kikuta, Kenji; Muraoka, Hiroyuki; Saito, Fumihito; Sato, Ryo

doi:10.1016/j.tetlet.2006.02.122

Cited by 17 publications

(6 citation statements)

References 36 publications

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“…The synthesis of 3‐BTBA ( 2 ) is shown in Scheme 1. Bromination of 7 with molecular bromine at room temperature resulted in the dibrominated compound ( 8 ; 51). The bromo group at the 2‐position was removed with butyl lithium at −78 °C resulting in compound 9.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Dual Wavelength Fluorescent Benzo[b]thiophene Boronic Acid Derivatives for Sugar Sensing

et al. 2007

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Cell surface glycoproteins have been known to play very important roles in various physiologic and pathologic processes. Small molecule compounds capable of carbohydrate recognition can be very useful for the development of sensing, diagnostic, and therapeutic agents. Along this line, we are interested in developing water-soluble fluorescent boronic acid compounds for carbohydrate recognition. As such, a series of benzo[b]thiophene boronic acid derivatives have been synthesized and their fluorescent properties analyzed at physiologic pH. Benzo[b]thiophene derivatives were found to be a new type of fluorescent reporter compounds capable of dual fluorescent emission under physiologic pH conditions. Compounds 1, 3, 4, 5, and 6 showed unusual emission wavelength shifts upon binding of sugars. These boronic acids will be useful tools for building glycoprotein biosensors for biologic applications.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Dual Wavelength Fluorescent Benzo[b]thiophene Boronic Acid Derivatives for Sugar Sensing

et al. 2007

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“…In order to study the influence of varying electron density at the five-membered heterocyclic ring on the electron transfer properties between the Fc/Fc + moieties a setup that allows electronic modification of the heterocyclic core without changing the geometry is significantly advantageous, because it enables a better comparability of the electrochemical results, as the electrostatic repulsion does not change within the respective series of compounds. Ogawa and Sato have shown that a modification of the electronic characteristics of the heterocycle itself, by either extending the π system or changing the heteroatom, can increase the redox separation of the attached redox-active ferrocenyl termini in, for example, 1,3-diferrocenylbenzo[ c ]thiophene ( 10 ) and 1,3-diferrocenylbenzo[ c ]selenophene ( 11 ), respectively (Chart ) . In comparison with diferrocenylthiophene ( 3 ), diferrocenylbenzo[ c ]thiophene ( 10 ) shows an increase in the redox separation of about 130 mV under identical measurement conditions ( 3 , Δ E °′ = 150 mV; 10 , Δ E °′ = 280 mV; supporting electrolyte [N n Bu 4 ][PF 6 ], c = 0.1 mol L –1 , dichloromethane).…”

Section: Electronic Modification Of the Heterocyclic Connecting Unitmentioning

confidence: 99%

(Multi)ferrocenyl Five-Membered Heterocycles: Excellent Connecting Units for Electron Transfer Studies

2013

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The electro- and spectroelectrochemical behavior of diverse (multi)ferrocenyl five-membered heterocyclic compounds, including furan, thiophene, pyrroles, phospholes, etc. is discussed, giving a close insight into the electron transfer processes of these organometallic compounds in their mixed-valence state, whereby electronic and structural modification of the heterocyclic connecting units and/or of the redox-active ferrocenyl termini directly influences the electron transfer properties. In addition, the structural features of these compounds can be correlated with their electrochemical behavior, allowing calculation of the effective electron transfer distance within a specific series of molecules. Tendencies in molecular wire molecules based on bi-, ter-, quarter-, quinque-, and sexithiophene connecting building blocks and the appropriate pyrrole derivatives are discussed as well. The consequences of introducing an additional redox-active transition-metal building block, such as a titanocene or a zirconocene moiety, respectively, into the heterocyclic ring, on the electrochemical behavior of the resulting five-membered heterocycles are also highlighted.

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“…In this research field, the object of our investigation is the construction of a new type of multi‐step multi‐electron redox system by utilizing the multi‐ferrocene derivatives bridged by a π‐conjugated spacer, including both an oxidation process of the multi‐ferrocene segments (organometallic redox‐active center) and oxidation and/or reduction processes of a π‐conjugated spacer (organic redox‐active center) . Our current efforts have focused on the synthesis and evaluation of the electrochemical properties of multi‐ferrocene derivatives bridged by an α‐oligothiophene spacer based on the following reasons.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical studies of the multi‐step multi‐electron redox process of tetraferrocenyloligothiophenes with electron donor and acceptor abilities

Muraoka

Ozawa

Ogawa

2018

Heteroatom Chemistry

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We have designed and synthesized tetraferrocenyloligothiophenes, namely, 4,4′5,5′‐tetraferrocenyl‐2,2′‐bithiophene (TFBT) and 4,4″,5,5″‐tetraferrocenyl‐2,2′:5′,2″‐terthiophene (TFTT). By using an electrochemical technique, we revealed that tetraferrocenyloligothiophenes show multi‐redox reactions derived from four ferrocene fragments and one α‐oligothiophene spacer, and a number of the thiophene rings in the α‐oligothiophene spacer can be attuned to the redox potentials and the multiple electron transfer process. Consequently, we have succeeded in the construction of different types of multi‐step multi‐electron redox systems by constructing four organometallic redox‐active ferrocenes and one organic redox‐active α‐oligothiophene differing in the number of thiophene rings.

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Synthesis, structure, and both cathodic and anodic reversible redox reactions of benzochalcogenophenes containing ferrocene units

Cited by 17 publications

References 36 publications

Synthesis and Evaluation of Dual Wavelength Fluorescent Benzo[b]thiophene Boronic Acid Derivatives for Sugar Sensing

Synthesis and Evaluation of Dual Wavelength Fluorescent Benzo[b]thiophene Boronic Acid Derivatives for Sugar Sensing

(Multi)ferrocenyl Five-Membered Heterocycles: Excellent Connecting Units for Electron Transfer Studies

Electrochemical studies of the multi‐step multi‐electron redox process of tetraferrocenyloligothiophenes with electron donor and acceptor abilities

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