5471-63-6

Usage

Uses

1. Used in Research and Development:
1,3-Diphenylisobenzofuran is used as a research chemical for its unique fluorescent properties and its role as a model compound in singlet fission studies.
2. Used in Detection of Superoxide Anion Radical:
1,3-Diphenylisobenzofuran is used as a fluorescent probe for the detection of superoxide anion radical (O2?) inside the membrane lipid layer through the DPBF fluorescence quenching method.
3. Used in Photoinactivation Studies:
1,3-Diphenylisobenzofuran is used as a quencher during the photoinactivation of TA-3 mouse mammary carcinoma cells containing hematoporphyrin, contributing to the understanding of cancer cell behavior under specific conditions.
4. Used in Structural and Photophysical Property Studies:
1,3-Diphenylisobenzofuran is employed to study the single crystal molecular structure and solution photophysical properties of DPBF, providing valuable insights into its behavior and potential applications in various fields.

Purification Methods

Recrystallise it from EtOH or EtOH/CHCl3 (1:1) under red light (as in photographic dark rooms) or from *benzene in the dark. [Beilstein 17/2 V 503.]

InChI:InChI=1/C20H20N4O2/c1-5-22-13(3)19-12(2)21-23-11-16(10-18(23)20(19)14(22)4)15-7-6-8-17(9-15)24(25)26/h6-11H,5H2,1-4H3

Upstream product

• 4746-79-6 1-(2'-benzoylphenyl)-2-phenylethane-1,2-dione 
• 421551-02-2 2-nitro-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene 
• 64836-60-8 2,2-Dimethyl-1,3-diphenylisoindene 
• 128225-26-3 C₅₂H₄₀O₆ 
• 92686-68-5 C₂₈H₂₂O 
• 66933-96-8 1,4-Diphenyl-2,3-dibenzoyl-1,4-dihydro-1,4-epoxynaphthalene 
• 21596-49-6 1,3-dihydro-1,3-diphenyl-isobenzofuran 
• 105941-87-5 N’-((2-bromophenyl)-(phenyl)methylene)-4-methylbenzenesulfonohydrazide 
• 98-88-4 benzoyl chloride 
• 128425-68-3 7,9-Diphenyl-8-oxa-tricyclo[4.3.0.0^7,9]nona-1,3,5-triene 
• 128425-67-2 7,8-Diphenyl-bicyclo[4.2.0]octa-1,3,5-triene-7,8-diol 
• 74563-17-0 C₂₀H₁₄O^(2-)*2Na⁽¹⁺⁾ 
• 74-88-4 methyl iodide 
• 797-98-8 2,3-diphenyl-2,3-epoxy-1-indanone 

Downstream Products

• 19061-38-2 (9s,10s)-9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene 
• 872297-33-1 3-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carbaldehyde 
• 421551-02-2 2-nitro-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene 
• 39495-59-5 2-nitro-1,3,4-triphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene 
• 872297-32-0 3-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carboxylic acid 
• 112046-30-7 (+/-)-1,4-diphenyl-1,2,3,4-tetrahydro-1r,4c-epoxido-naphthalene-2ξ-carbonitrile 
• 24344-71-6 10,15-Diphenyl-10,15-dihydro-10,15-epoxido-benzo[f]phenanthro[9,10-b][1,4]dioxocin 
• 872297-31-9 3-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carboxylic acid ethyl ester 
• 25914-44-7 5,10-diphenyl-11H-benzofluorene 
• 872297-34-2 1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carbaldehyde 
• 856364-85-7 1,4-diphenyl-1,4-dihydro-1,4-epoxido-naphthalene-2,3-dicarboxylic acid diethyl ester 
• 13093-44-2 7,12-diphenyl-(6br,12ac)-6b,7,12,12a-tetrahydro-7ξ,12ξ-epoxido-benzo[k]fluoranthene 
• 16391-62-1 (7,12-diphenyl)benzofluoranthene 
• 74012-50-3 1,3,4-triphenyl-[2]naphthoic acid ethyl ester 

Relevant academic research and scientific papers

POLYCYCLIC AROMATIC COMPOUND AND ORGANOELECTROLUMINESCENT DEVICE USING THE SAME

Disclosed is a polycyclic aromatic compound that can be employed in an organic layer of an organic electroluminescent device. Also disclosed is a highly efficient organic electroluminescent device including the polycyclic aromatic compound. The use of the polycyclic aromatic compound significantly improves the luminous efficiency of the device.

Reductive coupling between aromatic aldehydes and ketones or imines by copper catalysis

The copper-catalyzed reductive coupling of two different carbonyl compounds has been achieved. The reaction of aromatic aldehydes and arylketones with a silylboronate in the presence of a catalytic amount of a CuCl-N-heterocyclic carbene (NHC) complex and a stoichiometric amount of alkoxide base yielded cross-coupled 1,2-diol derivatives. A reaction pathway is proposed that involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species from the aromatic aldehyde and its subsequent coupling with the arylketone. This process was amenable to asymmetric catalysis. This copper catalyst system also enabled the reductive coupling between aromatic aldehydes and imines.

A One-pot preparation of 1,3-diarylisobenzofuran

A simple, practical, and efficient method for one-pot synthesis of symmetric and unsymmetrical 1,3-diarylisobenzofurans has been developed by sequential reactions of methyl 2-formylbenzoate with two identical or different aryl metal species.

Toward designed singlet fission: Solution photophysics of two indirectly coupled covalent dimers of 1,3-diphenylisobenzofuran

In order to identify optimal conditions for singlet fission, we are examining the photophysics of 1,3-diphenylisobenzofuran (1) dimers covalently coupled in various ways. In the two dimers studied presently, the coupling is weak. The subunits are linked via the para position of one of the phenyl substituents, in one case (2) through a CH2 linker and in the other (3) directly, but with methyl substituents in ortho positions forcing a nearly perpendicular twist between the two joint phenyl rings. The measurements are accompanied with density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations. Although in neat solid state, 1 undergoes singlet fission with a rate constant higher than 1011 s-1; in nonpolar solutions of 2 and 3, the triplet formation rate constant is less than 106 s-1 and fluorescence is the only significant event following electronic excitation. In polar solvents, fluorescence is weaker because the initial excited singlet state S1 equilibrates by sub-nanosecond charge transfer with a nonemissive dipolar species in which a radical cation of 1 is attached to a radical anion of 1. Most of this charge transfer species decays to S0, and some is converted into triplet T1 with a rate constant near 108 s-1. Experimental uncertainties prevent an accurate determination of the number of T1 excitations that result when a single S1 excitation changes into triplet excitation. It would be one if the charge-transfer species undergoes ordinary intersystem crossing and two if it undergoes the second step of two-step singlet fission. The triplet yield maximizes below room temperature to a value of roughly 9% for 3 and 4% for 2. Above a??360 K, some of the S1 molecules of 3 are converted into an isomeric charge-transfer species with a shorter lifetime, possibly with a twisted intramolecular charge transfer (TICT) structure. This is not observed in 2. ? 2013 American Chemical Society.

Facile Sc(OTf)3-catalyzed generation and successive aromatization of isobenzofuran from o -dicarbonylbenzenes

Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels-Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

Facile synthesis of dihaloheterocycles via electrophilic iodocyclization

An efficient and facile electrophilic iodocyclization for the synthesis of various O-, N-, and S-containing dihaloheterocycles has been developed. A wide range of the substituted propargyl alcohols having -OH, -NTs, and -SAc functional groups reacted with molecular iodine or bromoiodine at ambient temperature to produce the corresponding dihalogenated O-, N-, and S-containing five- and six-membered heterocycles in good to high yields; Under optimized solvent conditions, the reactions of various substituted but-2-yn-1-ones bearing -OH, -NTs, and -SAc functional groups at C4-position, with iodine or bromoiodine at ambient temperature afforded the corresponding 3,4-diiodo- and 3-bromo-4-iodo-substituted furans, pyrroles, and thiophenes in good to high yields. Further transformation of the resulting iodine- or bromine-containing products to polyaromatics potentially of useful as organo-material intermediates has been investigated.

Regiospecific synthesis of functionalised 1,3-diarylisobenzofurans via palladium- and rhodium-catalysed reaction of boronic acids with o-acylbenzaldehydes under thermal or microwave activation

Variously substituted 1,3-diarylisobenzofurans have been regiospecifically prepared via palladium- and rhodium-catalysed reaction of functionalised boronic acids onto o-acylbenzaldehydes. Rhodium catalysis has furthermore been improved using microwave act

Cross-coupling reactions between C(sp2)-H and C(sp 3)-H bonds via sequential dehydrogenation and C-H insertion

Formal C(sp2)-H and C(sp3)-H cross-coupling reactions were carried out by iridium-catalyzed transfer dehydrogenation of primary alcohols and sequential manganese-catalyzed insertion of the formed aldehydes into a carbon-hydrogen bond of aromatic or olefinic compounds. Georg Thieme Verlag Stuttgart - New York.

A versatile and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans

(Chemical Equation Presented) A convenient, versatile, and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans has been developed. It involves chemoselective addition of arylmagnesium reagents to the aldehyde function of o-aroylbenzaldehydes, themselves readily obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. Various functional groups, including nitro, iodo, or ester functionalities, have thus been positioned with complete regiospecificity on the 1,3-diphenylisobenzofuran backbone.

Synthesis and characterization of 1,3-diarylbenzo[c]selenophenes

A series of 1,3-diarylbenzo[c]selenophenes (symmetrical/unsymmetrical) have been synthesized involving a selenium transfer reaction of keto-alcohol/benzo[c]furan using Woollins reagent. The optical and electrochemical studies of these diarylbenzo[c]selenophenes are correlated with their structures.