Synthesis, Structures, and Temperature-Dependent Photoluminescence of 1,4-Diphenyl-1-telluro-1,3-butadiene Incorporated in a Dibenzobarrelene Skeleton and Derivatives

被引：22

作者：

Annaka, Tatsuro ^{[1
]}

Nakata, Norio ^{[1
]}

Ishii, Akihiko ^{[1
]}

机构：

[1] Saitama Univ, Dept Chem, Grad Sch Sci & Engn, Sakura Ku, Saitama 3388570, Japan

来源：

ORGANOMETALLICS | 2015年 / 34卷 / 07期

基金：

日本学术振兴会;

关键词：

CENTER-DOT-BR; CRYSTAL-STRUCTURE; RIGID DIBENZOBARRELENE; EXCITATION-ENERGIES; FACILE SYNTHESIS; FLUORESCENCE; TELLURIUM; SELENIUM; SYSTEMS; OXYGEN;

D O I：

10.1021/acs.organomet.5b00016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1,4-Diphenyl-1-telluro-1,3-butadiene incorporated in a dibenzobarrelene skeleton was synthesized with a good yield by an intramolecular DielsAlder reaction of the corresponding 1-(9-anthyltelluro)enyne. Oxidation and bromination of the telluride yielded telluroxide and hypervalent Te,Te-dibromide, respectively. Their structures were determined by X-ray crystallography. Unlike its highly fluorescent sulfur and selenium congeners, the telluride is barely fluorescent in solution at room temperature due to the heavy-atom effect of tellurium. The telluride displayed temperature-dependent fluorescence; it is fluorescent with a moderate quantum yield (Phi(PL) = 0.42) in the glass of 2-methyltetrahydrofuran at 77 K.

引用

页码：1272 / 1278

页数：7

共 48 条

[1]

Ahlrichs R., 1996, CHEM PHYS LETT, V266, P454

[2]

Akiba K.-y., 2011, ORGANO MAIN GROUP CH, P33

[3]

Alock N. W., 1982, J CHEM SOC DA, V1982, P709

[4] Synthesis and Photophysical Properties of Extended π-Conjugative and Push-Pull-Type 1,4-Diaryl-1-thio-1,3-butadienes Incorporated in a Dibenzobarrelene Skeleton [J].

Annaka, Tatsuro ;

Nakata, Norio ;

Ishii, Akihiko .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (04) :554-561

[5] New insights into the structures of diorganotellurium oxides.: The first polymeric diorganotelluroxane [(p-MeOC6H4)2TeO]n [J].

Beckmann, J ;

Dakternieks, D ;

Duthie, A ;

Ribot, F ;

Schürmann, M ;

Lewcenko, NA .

ORGANOMETALLICS, 2003, 22 (16) :3257-3261

[6] RADIATIONLESS DEACTIVATION OF FLUORESCENT STATE OF SUBSTITUTED ANTHRACENES [J].

BENNETT, RG ;

MCCARTIN, PJ .

JOURNAL OF CHEMICAL PHYSICS, 1966, 44 (05) :1969-&

[7] THE EFFECT OF TEMPERATURE ON FLUORESCENCE OF SOLUTIONS [J].

BOWEN, EJ ;

SAHU, J .

JOURNAL OF PHYSICAL CHEMISTRY, 1959, 63 (01) :4-5

[8] Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes [J].

Carrera, Elisa I. ;

Seferos, Dwight S. .

DALTON TRANSACTIONS, 2015, 44 (05) :2092-2096

[9] Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold [J].

Casida, ME ;

Jamorski, C ;

Casida, KC ;

Salahub, DR .

JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (11) :4439-4449

[10] Unsymmetrical 1-naphthyltellurium(IV) dihalides:: the interplay of Te•••Br, C-H•••Br and C-H•••π interactions in the crystal structure of (1-naphthyl)(4-methylphenyl)tellurium(IV) dibromide [J].

Chauhan, Ashok K. S. ;

Kumar, Arun ;

Srivastava, Ramesh C. ;

Butcher, Ray J. .

STRUCTURAL CHEMISTRY, 2007, 18 (02) :181-186

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