Hexasubstituted Benzenes with Ultrastrong Dipole Moments

被引：75

作者：

Wudarczyk, Jakob ^{[1
]}

Papamokos, George ^{[2
]}

Margaritis, Vasilis ^{[2
]}

Schollmeyer, Dieter ^{[3
]}

Hinkel, Felix ^{[1
]}

Baumgarten, Martin ^{[1
]}

Floudas, George ^{[2
]}

Muellen, Klaus ^{[1
]}

机构：

[1] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany

[2] Univ Ioannina, Dept Phys, POB 1186, GR-45110 Ioannina, Greece

[3] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 09期

关键词：

aromatic substitution; dielectric spectroscopy; dihydrobenzimidazoles; dipole moments; donor-acceptor systems; CORRELATED MOLECULAR CALCULATIONS; ORGANIC SOLAR-CELLS; GAUSSIAN-BASIS SETS; DENSITY; POLARIZABILITIES; ENERGY; CHROMOPHORES; OXIDANTS; HYDROGEN;

D O I：

10.1002/anie.201508249

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hexasubstituted benzenes have been synthesized with the highest known dipole moments, as determined by dielectric spectroscopy and DFT methods. Based on the preparation of 4,5-diamino-3,6-dibromophthalonitrile, combined with a novel method to synthesize dihydrobenzimidazoles, these benzene derivatives have dipole moments in excess of 10debye. Such dipole moments are desirable in ferroelectrics, nonlinear optics, and in organic photovoltaics. Structure determination was achieved through single-crystal X-ray crystallography, and the optical properties were determined by UV/Vis absorption and fluorescence spectroscopy.

引用

页码：3220 / 3223

页数：4

共 35 条

[1] Cyanated perylene-3,4-dicarboximides and perylene-3,4:9,10-bis(dicarboximide):: Facile chromophoric oxidants for organic photonics and electronics [J].

Ahrens, MJ ;

Fuller, MJ ;

Wasielewski, MR .

CHEMISTRY OF MATERIALS, 2003, 15 (14) :2684-2686

[2]

[Anonymous], 2011, Angew. Chem, DOI DOI 10.1002/ANGE.201002307

[3] Organic ferroelectric opto-electronic memories [J].

Asadi, Kamal ;

Li, Mengyuan ;

Blom, Paul W. M. ;

Kemerink, Martijn ;

de Leeuw, Dago M. .

MATERIALS TODAY, 2011, 14 (12) :592-599

[4] Simple and efficient chlorination and bromination of aromatic compounds with aqueous TBHP (or H2O2) and a hydrohalic acid. [J].

Barhate, NB ;

Gajare, AS ;

Wakharkar, RD ;

Bedekar, AV .

TETRAHEDRON LETTERS, 1998, 39 (35) :6349-6350

[5] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[6]

Böttcher CJF, 1943, RECL TRAV CHIM PAY-B, V62, P119

[7] Mind the gap! [J].

Bredas, Jean-Luc .

MATERIALS HORIZONS, 2014, 1 (01) :17-19

[8] Pushing the Envelope of the Intrinsic Limitation of Organic Solar Cells [J].

Camaioni, Nadia ;

Po, Riccardo .

JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2013, 4 (11) :1821-1828

[9] Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers [J].

Casey, Abby ;

Han, Yang ;

Fei, Zhuping ;

White, Andrew J. P. ;

Anthopoulos, Thomas D. ;

Heeney, Martin .

JOURNAL OF MATERIALS CHEMISTRY C, 2015, 3 (02) :265-275

[10] EXPERIMENTAL INVESTIGATIONS OF ORGANIC MOLECULAR NONLINEAR OPTICAL POLARIZABILITIES .1. METHODS AND RESULTS ON BENZENE AND STILBENE DERIVATIVES [J].

CHENG, LT ;

TAM, W ;

STEVENSON, SH ;

MEREDITH, GR ;

RIKKEN, G ;

MARDER, SR .

JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (26) :10631-10643

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