Highly selective conversion of hydroxylated biaryls to dibenzofuran derivatives over zeolite catalyst

Arienti, A.; Bigi, Franca; Maggi, Raimondo; Moggi, P.; Rastelli, Massimo; Sartori, Giovanni; Trere, A.

doi:10.1039/a607282h

Cited by 33 publications

(16 citation statements)

References 8 publications

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“…[18] We found that the cheap and commercially available HY Zeolith CBV400 (Zeolyst International) could also be used for the pyrolytic dehydration of BINOL in place of the originally suggested Zeolite HSZ 360 (Tosoh). The target product 5 was obtained in good yield (90 %) in o-dichlorobenzene at reflux.…”

Section: Results and Discussion A) Synthesismentioning

confidence: 99%

“…The compound was prepared by a modification of the procedure of Sartori et al [18] A mixture of rac-BINOL (2.00 g, 6.99 mmol) and Zeolith CBV400 (Zeolyst International, 1.10 g) in o-dichlorobenzene (15 mL) was heated at reflux for 5 h with stirring. After cooling to room temperature, the resulting pale-brown suspension was filtered off and the yellow solution was evaporated.…”

Section: Dinaphtho[21-b;1ј2ј-d]furan (5)mentioning

confidence: 99%

“…By the methods of Kadyrov and Heinicke [17] or of Sartori, [18] rac-BINOL can be converted into dinaphtho[2,1-b; 1Ј,2Ј-d]furan (5). We assumed that dilithiation of 5 could open the furan ring as already shown in a related protocol with benzofuran [17] and should thus afford the dilithiated compound 6.…”

Section: Introductionmentioning

confidence: 99%

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A Highly Diastereoselective Route to Dinaphtho[c,e][1,2]oxaphosphinines and Their Application as Ligands in Homogeneous Catalysis

et al. 2010

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Keywords: Phosphane ligands / P ligands / Density functional calculations / HydroformylationA new and facile method for the synthesis of 6H-dinaphtho-[c,e][1,2]oxaphosphinines starting from dinaphthol (BINOL) is described. The ring-opening of an intermediary dinaphtho[2,1-b;1Ј,2Ј-d]furan proceeds with extremely high diastereoselectivity and forms the thermodynamically most stable product. The stereochemistry was elucidated by 31 P NMR spectroscopy and X-ray structural analysis. Epimerization at the stereogenic P-centre did not take place. DFT calculations were performed to determine the dihedral

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Section: Results and Discussion A) Synthesismentioning

confidence: 99%

Section: Dinaphtho[21-b;1ј2ј-d]furan (5)mentioning

confidence: 99%

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A Highly Diastereoselective Route to Dinaphtho[c,e][1,2]oxaphosphinines and Their Application as Ligands in Homogeneous Catalysis

et al. 2010

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“…3,7 The starting materials, 2-methoxy-6-phenylnaphthalene and 2-methoxy-7-phenylnaphthalene, were prepared according to procedures reported in the literature. 8 The synthetic route used for Ph-DNF-VW is depicted in Scheme 1: 2-methoxy-7-phenylnaphthalene was selectively deprotonated with n-BuLi, followed by an oxidative homocoupling reaction with Fe(acac) 3 to produce 3,3¤-dimethoxy-6,6¤-diphenyl-2,2¤-binaphthalene.…”

Section: ¹1mentioning

confidence: 99%

Impact of Phenyl Groups on Oxygen-bridged V-shaped Organic Semiconductors

Mitsui¹,

Kubo²,

Tanaka³

et al. 2017

Chem. Lett.

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We have developed two novel, isomeric compounds of phenyl-substituted dinaphtho [2,3-b:2¤,3¤-d]furan (Ph-DNF-VW and Ph-DNF-VV) using a facile synthetic protocol. Notably, Ph-DNF-VW has been shown to be a strong candidate for lightemitting device applications: it forms a herringbone-packing structure with effective CH£π interactions between phenyl moieties, and exhibits a high thermal stability in the crystal phase in air and a high fluorescence quantum yield in the solid state. Additionally, its carrier mobility is comparable to that of amorphous silicon.Keywords: V-shaped organic semiconductor | Sky-blue emission | Organic field-effect transistor (OFET)Organic semiconducting materials have attracted great interest as active layers for next-generation printable and flexible electronic devices. A large number of carrier-transporting materials based on π-electron-conjugated molecules have been developed, exhibiting mobilities greater than those of amorphous silicon (0.51.0 cm 2 V ¹1 s ¹1 ). Additional functionalities such as luminescence 1 and sensing 2 are fascinating characteristics in organic semiconductors, and have been areas of focus in recent research. Recently, we developed an oxygen-bridged, V- Figure 1), which exhibits a high mobility (up to 1.1 cm 2 V ¹1 s ¹1) and blue-emissive characteristics with a high quantum efficiency (Φ F = 72%) even in the solid state, 3 whereas the sulfur-bridged congener exhibits very weak photoluminescence with Φ F of lower than 3%.This light-element, oxygen-bridged core structure could provide a framework for the synthesis of further materials that may be applicable as light emitters in organic light-emitting diodes (OLEDs) 4 or transistors (OLETs). 5 Furthermore, the addition of alkyl chains to these structures aids the solution processing of the materials and promotes the precise control of aggregate structures that are desirable for effective charge transport. However, alkylated DNF-Vs showed a rather low emission efficiency compared to the parent DNF-V species, probably because the changes in structural dynamics induced by the presence of the long, flexible alkyl chains led to an overall increase in the nonradiative decay rate constant. In this work, we focus on the replacement of flexible alkyl chains with rigid phenyl substituents. 6 As well as altering the structural properties, the phenyl substituents can also elevate the HOMO energy level by extending π-conjugation over the system: this may yield improvements in device performance over the parent DNF-V species, specifically in charge-carrier injection from the electrodes, and in the threshold voltage in organic field-effect transistors (OFETs). In this paper, we describe facile synthesis of two isomeric, phenyl-substituted DNF-V derivatives, where the phenyl groups are located at either the 3,9-or 2,10-positions on the DNF-V core (the two compounds are hereafter referred to as Ph-DNF-VW and Ph-DNF-VV as shown in Figure 1). We clarify the influence of the substitution position on their crystal structures, and on the...

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“…In this synthetic methodology, the overall yields of alkyl substituted DNF-Vs, regardless of the positions and lengths of the alkyl chains, were 40-67%. 16 Single crystal structure analysis Using the crystal structures of DNF-V derivatives reported previously, 14 we discuss the packing structures and their carrier transporting abilities more in detail. Note that DNF-V derivatives assemble in herringbone packing motifs and their core structures are slightly bent, with the dihedral angle of 4.00-8.98°between two naphthalene units in a single crystal, as illustrated in Figure 2a-c.…”

Section: Synthesismentioning

confidence: 99%

Alkylated oxygen-bridged V-shaped molecules: impacts of the substitution position and length of the alkyl chains on the crystal structures and fundamental properties in aggregated forms

Mitsui

Annaka

Nakamura

et al. 2016

Polym J

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We have recently developed dinaphtho [2,3-b:2',3'-d]furan (DNF-V) derivatives as a new type of solution-processable organic semiconducting material with high carrier mobility and high emission efficiency in the solid state. In this article, we systematically investigate and reveal the impact of the substitution position and the length of the alkyl side chains on their physicochemical properties based on their packing structures. For both alkylated DNF-VV and DNF-VW derivatives, the solubilities and the phase-transition temperatures increase as the shorter alkyl chains are attached. In particular, alkylated DNF-VV simultaneously achieve high solubility (over 1 wt%) and a highly stabilized crystal phase (up to 199°C). Furthermore, DNF-V derivatives exhibit a deep-blue emission in the solid state with a quantum efficiency ranging from 17 to 51%. Such a range of physicochemical properties is probably related to the dependencies on the molecular geometry in the crystal state and the length of the alkyl side chains.

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Highly selective conversion of hydroxylated biaryls to dibenzofuran derivatives over zeolite catalyst

Cited by 33 publications

References 8 publications

A Highly Diastereoselective Route to Dinaphtho[c,e][1,2]oxaphosphinines and Their Application as Ligands in Homogeneous Catalysis

A Highly Diastereoselective Route to Dinaphtho[c,e][1,2]oxaphosphinines and Their Application as Ligands in Homogeneous Catalysis

Impact of Phenyl Groups on Oxygen-bridged V-shaped Organic Semiconductors

Alkylated oxygen-bridged V-shaped molecules: impacts of the substitution position and length of the alkyl chains on the crystal structures and fundamental properties in aggregated forms

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