[2,2′]Bi[naphtho[2,3-b]furanyl]: a versatile organic semiconductor with a furan–furan junction

Niimi, Kazuki; Mori, Hiroki; Miyazaki, Eigo; Osaka, Itaru; Kakizoe, Hayato; Takimiya, Kazuo; Adachi, Chihaya

doi:10.1039/c2cc31960h

Cited by 72 publications

(46 citation statements)

References 31 publications

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“…Takimiya 研究小组 [27] 还报道了首例基于呋喃有机半导体的 OLET(比 Bendikov 研究小组 [22] 报道的基于寡聚呋喃的 OLET 要早). 合成了二(萘并[2,3-b]呋喃)20 [27] , 并与噻吩类似物 21 [28] 做了比较研究. 20 与 21 的发光性质明显不同, 前者的量子效率比后者要高得多(0.88 vs 0.014).…”

Section: Compdunclassified

Furan Derivatives: An Emerging Class of Organic Semiconductors

Li¹

2015

Chin. J. Org. Chem.

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π-Conjugated molecules are widely used in the fields of organic field-effect transistors, organic solar cells, dye-sensitized solar cells and organic light-emitting diodes, etc. π-Conjugated furan derivatives have attracted widespread interest due to the high carrier mobility, high photoluminescent quantum efficiency and good solubility. It has been corroborated that furan derivatives are a class of good semiconducting materials by the experimental and theoretical research results. A furan ring is frequently integrated into π-conjugated molecules either by fusion with carbon π-system or by using as a π-linker, which significantly alters the photophysical, electrochemical and charge transporting properties of the π-conjugated molecules. Furan derivatives could be used to fabricate high performance organic field-effect transistors, organic solar cells, dye-sensitized solar cells and organic light-emitting diodes. In addition to a brief introduction of the characteristics of furan derivatives, the author introduced the research progress of the application of furan derivatives in the fields of organic field-effect transistors, organic solar cells, dye-sensitized solar cells and organic light-emitting diodes.

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Section: Compdunclassified

Furan Derivatives: An Emerging Class of Organic Semiconductors

Li¹

2015

Chin. J. Org. Chem.

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“…This pseudo‐halogen approach using a (trifluoromethyl)sulfonyloxy group can also be applied to the synthesis of NT and AT systems in which one thiophene ring is annulated at the 2,3‐bond of naphthalene or anthracene (Scheme ). In this synthesis, 2‐methoxy derivatives turned out to be very useful starting materials: selective lithiation at the 3‐position, assisted by the o ‐directing nature of the methoxy group, enabled the selective formation of 2‐bromo‐3‐methoxynaphthalene26 or ‐anthracene 9. The methoxy group was then converted (demethylation effected by BBr 3 ) into the (trifluoromethyl)sulfonyloxy group, which was similarly utilized in subsequent Sonogashira coupling and thienannulation to afford the desired NT or AT.…”

Section: Thienannulation Of Terminal Thiophene Ringsmentioning

confidence: 99%

Thienannulation: Efficient Synthesis of π‐Extended Thienoacenes Applicable to Organic Semiconductors

et al. 2012

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This microreview focuses on several thiophene‐annulation reactions of less cyclic precursors on aromatic units (“thienannulation reactions”), which have been applied to the synthesis of a range of π‐extended thienoacene‐based organic semiconductors. Those thienannulation reactions can be applicable to the syntheses of two types of fused‐thiophene compounds: those with terminal fused thiophene units, represented by acene(di)thiophenes such as benzo[1,2‐b:4,5‐b′]dithiophene (BDT), and those with internal thiophene units, such as [1]benzothieno[3,2‐b][1]benzothiophene (BTBT). In addition, this microreview discusses the merits, scope, and limitations of the thienannulation reactions and demonstrates their high reproducibility with different substrates. It also shows that the corresponding less cyclic precursor subunits for the thiophene‐fused substructures can be regarded as synthetic equivalents or “synthons” for certain types of thienoacene‐based organic semiconductors.

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“…Furan, as a ubiquitous organic frame, has been less studied than thiophene in the research of organic electronic [32][33][34][35]. The lack of interest may be attributed to the chemical instability of furan and its derivatives [36].…”

Section: Introductionmentioning

confidence: 97%