Shared posts

03 Aug 06:52

Visible Light Mediated Photoredox Catalytic Arylation Reactions

by Indrajit Ghosh, Leyre Marzo, Amrita Das, Rizwan Shaikh and Burkhard König

TOC Graphic

Accounts of Chemical Research
DOI: 10.1021/acs.accounts.6b00229
03 Aug 06:49

First-Generation Subporphyrinatoboron(III) Sensitizers Surpass the 10 % Power Conversion Efficiency Threshold

First‐Generation Subporphyrinatoboron(III) Sensitizers Surpass the 10 % Power Conversion Efficiency Threshold

Sensitivity training: The first generation of subporphyrinatoboron(III)-based molecular sensitizers were tested in dye-sensitized solar cells (DSSCs). The most advanced prototype achieved a photon-to-current conversion efficiency value of 10.1 %. Such an astonishing figure suggests the potential for subporphyrinatoboron compounds in the field of DSSCs.

[Communication]
Graeme Copley, Daesub Hwang, Dongho Kim, Atsuhiro Osuka
Angew. Chem. Int. Ed., August 02, 2016, DOI: 10.1002/anie.201604432. Read article

30 Jul 08:50

Synthesis and Photophysical Properties of Aza[n]helicenes

by Gourav M. Upadhyay, Harish R. Talele and Ashutosh V. Bedekar

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b01395
22 Jul 07:22

Formation of Curvature Subunit of Carbon in Combustion

by Xin-Zhou Wu, Yang-Rong Yao, Miao-Miao Chen, Han-Rui Tian, Jun Xiao, Yun-Yan Xu, Min-Song Lin, Laura Abella, Cheng-Bo Tian, Cong-Li Gao, Qianyan Zhang, Su-Yuan Xie, Rong-Bin Huang and Lan-Sun Zheng

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.6b04898
16 Jul 21:40

Metal-Assisted One-Pot Synthesis of Isoporphyrin Complexes

Metal‐Assisted One‐Pot Synthesis of Isoporphyrin Complexes

Old synthesis, new tricks: Isoporphyrins form in unprecedented amounts if the long-established Adler–Longo condensation for tetraarylporphyrin synthesis is performed in the presence of metal acetates as template agents. The isoporphyrins formed by this one-pot method are surprisingly stable and show the anticipated long-wavelength absorption typical for this class of porphyrinoids.

[Communication]
Peter Schweyen, Martin Hoffmann, Jens Krumsieck, Benedikt Wolfram, Xiulan Xie, Martin Bröring
Angew. Chem. Int. Ed., July 15, 2016, DOI: 10.1002/anie.201604297. Read article

07 Jul 08:50

Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines

Metal‐Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines

Triple two: A metal-free [2+2+2] cycloaddition of internal ynamides and nitriles was developed for the de novo synthesis of fully substituted pyridines. In contrast to metal catalysis, the versatile Brønsted acid HNTf2 smoothly catalyzes the mild intermolecular cyclotrimerization of a range of ynamides and unactivated nitriles with complementary chemoselectivity.

[Communication]
Yong Wang, Li-Juan Song, Xinhao Zhang, Jianwei Sun
Angew. Chem. Int. Ed., July 06, 2016, DOI: 10.1002/anie.201603889. Read article

17 Jun 21:01

Synthesis of an ABCD-Type Phthalocyanine by Intramolecular Cyclization Reaction

by Sun Y. S. Chow and Dennis K. P. Ng

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.6b01489
08 Jun 07:58

Electrophilic Aromatic Substitution: New Insights into an Old Class of Reactions

by Boris Galabov, Didi Nalbantova, Paul von R. Schleyer and Henry F. Schaefer

TOC Graphic

Accounts of Chemical Research
DOI: 10.1021/acs.accounts.6b00120
01 Jun 06:20

Helicenes as All-in-One Organic Materials for Application in OLEDs: Synthesis and Diverse Applications of Carbo- and Aza[5]helical Diamines

by Samik Jhulki, Abhaya Kumar Mishra, Tahsin J. Chow, Jarugu Narasimha Moorthy

Abstract

A set of eight helical diamines were designed and synthesized to demonstrate their relevance as all-in-one materials for multifarious applications in organic light-emitting diodes (OLEDs), that is, as hole-transporting materials (HTMs), EMs, bifunctional hole transporting + emissive materials, and host materials. Azahelical diamines function very well as HTMs. Indeed, with high Tg values (127–214 °C), they are superior alternatives to popular N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine (NPB). All the helical diamines exhibit emissive properties when employed in nondoped as well as doped devices, the performance characteristics being superior in the latter. One of the carbohelical diamines (CHTPA) serves the dual function of hole transport as well as emission in simple double-layer devices; the efficiencies observed were better by quite some margin than those of other emissive helicenes reported. The twisting endows helical diamines with significantly high triplet energies such that they also function as host materials for red and green phosphors, that is, [Ir(btp)2acac] (btp=2-(2′-benzothienyl)pyridine; acac=acetylacetonate) and [Ir(ppy)3] (ppy=2-phenylpyridine), respectively. The results of device fabrications demonstrate how helicity/ helical scaffold may be diligently exploited to create molecular systems for maneuvering diverse applications in OLEDs.

Thumbnail image of graphical abstract

Not only aesthetically beautiful, but also functionally charming! Helicity as a design element allows creation of new organic materials for multifarious applications in organic light-emitting diodes (OLEDs). Helical diamines are shown to function as hole-transporting (HTM), emissive (EM), hole-transporting+emissive, and host materials (see figure).

24 May 17:57

Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals

by Gabriel E. Rudebusch

Nature Chemistry. doi:10.1038/nchem.2518

Authors: Gabriel E. Rudebusch, José L. Zafra, Kjell Jorner, Kotaro Fukuda, Jonathan L. Marshall, Iratxe Arrechea-Marcos, Guzmán L. Espejo, Rocío Ponce Ortiz, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Henrik Ottosson, Juan Casado & Michael M. Haley

Biradical polycyclic hydrocarbons are promising materials for organic spintronic and photovoltaic applications. The efficient and scalable synthesis of a diindenoanthracene derivative that exhibits moderate biradical character, yet is remarkably stable towards oxygen and heat, is now reported. A thermally accessible magnetic triplet state was studied through variable temperature techniques.

21 May 08:09

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

by Indranirekha Saikia, Arun Jyoti Borah and Prodeep Phukan

TOC Graphic

Chemical Reviews
DOI: 10.1021/acs.chemrev.5b00400
21 May 08:07

“Planetary Orbit” Systems Composed of Cycloparaphenylenes

by Steven M. Bachrach and Zeina-Christina Zayat

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00339
03 May 12:19

Engineering Stacks of V-Shaped Polyaromatic Compounds with Alkyl Chains for Enhanced Emission in the Solid State

Engineering Stacks of V‐Shaped Polyaromatic Compounds with Alkyl Chains for Enhanced Emission in the Solid State

Stacking up: Two types of fluorescent solids were generated from a V-shaped bisanthracene derivative with three butyl groups. The highly emissive solid (ΦF= >70 %) adopts a head-to-head arrangement with discrete stacks of the anthracene moieties. Furthermore, large enhancements of dye emissions (up to 45-fold) were achieved in the solid state by adding various fluorescent dyes to the V-shaped compound.

[Communication]
Shoya Sekiguchi, Kei Kondo, Yoshihisa Sei, Munetaka Akita, Michito Yoshizawa
Angew. Chem. Int. Ed., April 28, 2016, DOI: 10.1002/anie.201602502. Read article

29 Apr 14:18

Chromene-Annulated Bacteriochlorins

by Michael A. Hyland, Nisansala Hewage, Kimberly Panther, Arunpatcha Nimthong-Roldán, Matthias Zeller, Milinda Samaraweera, José A. Gascon and Christian Brückner

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00273
29 Apr 14:02

Synthesis and Photophysical Properties of a 13,13′-Bibenzo[b]perylenyl Derivative as a π-Extended 1,1′-Binaphthyl Analog

by Yosuke Uchida, Takashi Hirose, Takuya Nakashima, Tsuyoshi Kawai and Kenji Matsuda

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.6b00747
20 Apr 09:04

Preparation of Azafullerene C59NR5 and Fullerene Derivative C60NAr5 with a Pyridine Moiety on the Cage Skeleton

by Ning Lou, Yanbang Li, Chengxing Cui, Yajun Liu and Liangbing Gan

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.6b00872
20 Apr 09:03

Dissymmetric Bis(dipyrrinato)zinc(II) Complexes: Rich Variety and Bright Red to Near-Infrared Luminescence with a Large Pseudo-Stokes Shift

by Ryota Sakamoto, Toshiki Iwashima, Julius F. Kögel, Shinpei Kusaka, Mizuho Tsuchiya, Yasutaka Kitagawa and Hiroshi Nishihara

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.6b02128
14 Apr 11:10

Synthesis of Di-peri-dinaphthoporphyrins by PtCl2-Mediated Cyclization of Quinodimethane-type Porphyrins

Synthesis of Di‐peri‐dinaphthoporphyrins by PtCl2‐Mediated Cyclization of Quinodimethane‐type Porphyrins

The core of the matter: Di-peri-dinaphthoporphyrins have been synthesized by PtCl2-mediated cycloisomerization reaction of quinodimethane-type porphyrins. These porphyrins can be regarded as a key substructure of fused porphyrinoids, for which a 24π antiaromatic circuit was proven to be a dominant resonance contributor by 1H NMR, UV/Vis absorption, cyclic voltammetry, NICS calculations, and AICD plot.

[Communication]
Masataka Umetani, Koji Naoda, Takayuki Tanaka, Seung-Kyu Lee, Juwon Oh, Dongho Kim, Atsuhiro Osuka
Angew. Chem. Int. Ed., April 13, 2016, DOI: 10.1002/anie.201601303. Read article

14 Apr 11:02

Hairpin Furans and Giant Biaryls

by Xin Geng, Joel T. Mague, James P. Donahue and Robert A. Pascal

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00492
14 Apr 10:57

Red to Near-Infrared Isoindole BODIPY Fluorophores: Synthesis, Crystal Structures, and Spectroscopic and Electrochemical Properties

by Changjiang Yu, Qinghua Wu, Jun Wang, Yun Wei, Erhong Hao and Lijuan Jiao

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00414
06 Apr 09:12

An Electron-Poor C64 Nanographene by Palladium-Catalyzed Cascade C−C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis

An Electron‐Poor C64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

Ten bonds in a single operation: The synthesis of an electron-poor nanographene with dicarboximide corners was accomplished by a palladium-catalyzed cascade process, forming ten C−C bonds in a single chemical operation. The planar geometry of this novel C64 nanographene was revealed by single-crystal X-ray analysis.

[Communication]
Sabine Seifert, Kazutaka Shoyama, David Schmidt, Frank Würthner
Angew. Chem. Int. Ed., April 05, 2016, DOI: 10.1002/anie.201601433. Read article

05 Apr 15:00

Solution Structures of Hauser Base iPr2NMgCl and Turbo-Hauser Base iPr2NMgCl·LiCl in THF and the Influence of LiCl on the Schlenk-Equilibrium

by Roman Neufeld, Thorsten L. Teuteberg, Regine Herbst-Irmer, Ricardo A. Mata and Dietmar Stalke

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.6b00345
22 Mar 09:31

A Solar Cell That Is Triggered by Sun and Rain

A Solar Cell That Is Triggered by Sun and Rain

A flexible solar cell that can be excited by sunlight and raindrops is presented. The solar-to-electric conversion efficiency is created by complicated photoelectrochemical reactions, while electric signals, produced by dropping raindrops on rGO film, arise from π-electron|cation pseudocapacitance at the rGO/raindrop interface. This work could guide the design of all-weather solar cells.

[Communication]
Qunwei Tang, Xiaopeng Wang, Peizhi Yang, Benlin He
Angew. Chem. Int. Ed., March 21, 2016, DOI: 10.1002/anie.201602114. Read article

22 Mar 09:28

Templated Synthesis of Single-Walled Carbon Nanotubes with Specific Structure

by Feng Yang, Xiao Wang, Meihui Li, Xiyan Liu, Xiulan Zhao, Daqi Zhang, Yan Zhang, Juan Yang and Yan Li

TOC Graphic

Accounts of Chemical Research
DOI: 10.1021/acs.accounts.5b00485
21 Mar 09:21

Synthesis and Shuttling Behavior of [2]Rotaxanes with a Pyrrole Moiety

by Yusuke Matsuoka, Yuichiro Mutoh, Isao Azumaya, Shoko Kikkawa, Takeshi Kasama and Shinichi Saito

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b02911
15 Mar 18:55

BODIPY-containing nanoscale metal-organic frameworks for photodynamic therapy

Chem. Commun., 2016, 52,5402-5405
DOI: 10.1039/C6CC01048B, Communication
Weiqi Wang, Lei Wang, Zhensheng Li, Zhigang Xie
BODIPY-immobilized metal-organic frameworks for photodynamic therapy were developed through solvent-assisted ligand exchange.
The content of this RSS Feed (c) The Royal Society of Chemistry
15 Mar 18:55

Rhodium-Catalyzed Stitching Reaction: Convergent Synthesis of Quinoidal Fused Oligosiloles

by Ryo Shintani, Ryo Iino and Kyoko Nozaki

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.6b00082
12 Mar 20:07

The Breaking and Mending of meso-Tetraarylporphyrins: Transmuting the Pyrrolic Building Blocks

by Christian Brückner

TOC Graphic

Accounts of Chemical Research
DOI: 10.1021/acs.accounts.6b00043
12 Mar 20:05

Boron-Catalyzed Aromatic C–H Bond Silylation with Hydrosilanes

by Yuanhong Ma, Baoli Wang, Liang Zhang and Zhaomin Hou

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.6b01349
10 Mar 16:06

Folding of ortho-Phenylenes

by C. Scott Hartley

TOC Graphic

Accounts of Chemical Research
DOI: 10.1021/acs.accounts.6b00038