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04 Sep 02:29

Tuning Singlet Fission in π-Bridge-π Chromophores

by Elango Kumarasamy, Samuel N. Sanders, Murad J. Y. Tayebjee, Amir Asadpoordarvish, Timothy J. H. Hele, Eric G. Fuemmeler, Andrew B. Pun, Lauren M. Yablon, Jonathan Z. Low, Daniel W. Paley, Jacob C. Dean, Bonnie Choi, Gregory D. Scholes, Michael L. Steigerwald, Nandini Ananth, Dane R. McCamey, Matthew Y. Sfeir and Luis M. Campos

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b05204
30 Aug 02:00

Contorted polycyclic aromatic hydrocarbons with cove regions and zig-zag edges

Chem. Commun., 2017, 53,8474-8477
DOI: 10.1039/C7CC03709K, Communication
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Yulan Chen, Tomasz Marszalek, Torsten Fritz, Martin Baumgarten, Manfred Wagner, Wojciech Pisula, Long Chen, Klaus Mullen
Three tetrapyrene-fused benzocoronenes were synthesized by a "bottom-up" approach, which offers a facile access to extended polycyclic aromatic hydrocarbons with cove regions and zig-zag edges.
The content of this RSS Feed (c) The Royal Society of Chemistry
30 Aug 01:22

Closed-shell paramagnetic porphyrinoids

Chem. Commun., 2017, 53,9866-9869
DOI: 10.1039/C7CC05232D, Communication
Rashid R. Valiev, Heike Fliegl, Dage Sundholm
Magnetizabilities and magnetically induced ring-current strength susceptibilities have been calculated at the Hartree-Fock, density functional theory and second order Moller-Plesset levels for a number of antiaromatic closed-shell carbaporphyrins, carbathiaporphyrins and isophlorins.
The content of this RSS Feed (c) The Royal Society of Chemistry
30 Aug 01:18

Porphyrinoid rotaxanes: building a mechanical picket fence

Chem. Sci., 2017, 8,6679-6685
DOI: 10.1039/C7SC03165C, Edge Article
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
T. H. Ngo, J. Labuta, G. N. Lim, W. A. Webre, F. D'Souza, P. A. Karr, J. E. M. Lewis, J. P. Hill, K. Ariga, S. M. Goldup
We demonstrate that the threaded macrocycles in interlocked porphyrin-corrole conjugates provide a mechanical "picket fence" without affecting their electronic properties.
The content of this RSS Feed (c) The Royal Society of Chemistry
03 Jul 11:06

Pentagon-Embedded Cycloarylenes with Cylindrical Shapes

Pentagon‐Embedded Cycloarylenes with Cylindrical Shapes

Multiple pentagons were synthetically embedded in cylinder-shaped molecules to obtain segments of haeckelite nanotubes with imperfect honeycomb arrays. In these cylinder-shaped molecules, conjugation was observed over the pentagon bridges. These compounds also provide intermediate structures for retrosynthetic analysis and inspiration for novel defective carbon nanotubes.

[Communication]
Shunpei Hitosugi, Sota Sato, Taisuke Matsuno, Takashi Koretsune, Ryotaro Arita, Hiroyuki Isobe
Angew. Chem. Int. Ed., June 29, 2017, https://doi.org/10.1002/anie.201704676 Read article

03 Jul 11:05

Cyclopenta Ring Fused Bisanthene and Its Charged Species with Open-Shell Singlet Diradical Character and Global Aromaticity/ Anti-Aromaticity

Cyclopenta Ring Fused Bisanthene and Its Charged Species with Open‐Shell Singlet Diradical Character and Global Aromaticity/ Anti‐Aromaticity

Good character: Cyclopenta ring fused bisanthene (middle) was facilely synthesized and shows global anti-aromaticity with moderate diradical character. The dication exhibits a unique [10]annulene-within-[18]annulene structure with an open-shell singlet ground state, while the dianion is a closed shell and displays a diatropic ring current on the π-conjugated periphery.

[Communication]
Qing Wang, Tullimilli Y. Gopalakrishna, Hoa Phan, Tun Seng Herng, Shaoqiang Dong, Jun Ding, Chunyan Chi
Angew. Chem. Int. Ed., June 29, 2017, https://doi.org/10.1002/anie.201704805 Read article

03 Jul 11:04

Thermal Disproportionation of Oxo-Functionalized Graphene

Thermal Disproportionation of Oxo‐Functionalized Graphene

Losing O's: Graphene can be prepared by heating oxo-functionalized graphene. Defunctionalization resulting in graphene formation (path I) is the dominant process.

[Communication]
Fabian Grote, Christoph Gruber, Felix Börrnert, Ute Kaiser, Siegfried Eigler
Angew. Chem. Int. Ed., June 30, 2017, https://doi.org/10.1002/anie.201704419 Read article

03 Jul 10:59

"Inverted" porphyrins: a distorted adsorption geometry of free-base porphyrins on Cu(111)

Chem. Commun., 2017, 53,8207-8210
DOI: 10.1039/C7CC04182A, Communication
Michael Lepper, Julia Kobl, Tobias Schmitt, Martin Gurrath, Abner de Siervo, M. Alexander Schneider, Hans-Peter Steinruck, Bernd Meyer, Hubertus Marbach, Wolfgang Hieringer
Peculiar "inverted" intramolecular conformation of a free-base porphyrin due to specific attractive molecule-substrate interaction.
The content of this RSS Feed (c) The Royal Society of Chemistry
03 Jul 10:58

Configurational Stability of [5]Helicenes

by Prince Ravat, Rahel Hinkelmann, David Steinebrunner, Alessandro Prescimone, Ina Bodoky and Michal Juríček

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Organic Letters
DOI: 10.1021/acs.orglett.7b01461
29 Jun 02:00

The K-Region in Pyrenes as a Key Position to Activate Aggregation-Induced Emission: Effects of Introducing Highly Twisted N,N-Dimethylamines

by Shunsuke Sasaki, Satoshi Suzuki, Kazunobu Igawa, Keiji Morokuma and Gen-ichi Konishi

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00996
24 Jun 08:44

Porphyrin Arch-Tapes: Synthesis, Contorted Structures, and Full Conjugation

by Norihito Fukui, Taeyeon Kim, Dongho Kim and Atsuhiro Osuka

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b05332
16 Jun 00:40

Pyreniporphyrins: Porphyrin Analogues That Incorporate a Polycyclic Aromatic Hydrocarbon Subunit within the Macrocyclic Framework

by Ruixiao Gao, Deyaa I. AbuSalim and Timothy D. Lash

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00829
02 Jun 23:22

Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence

by Bettina D. Gliemann, Volker Strauss, Jakob F. Hitzenberger, Pavlo O. Dral, Frank Hampel, Jean-Paul Gisselbrecht, Thomas Drewello, Walter Thiel, Dirk M. Guldi, Milan Kivala

Abstract

We describe the synthesis as well as the electronic and photophysical characterization of novel N-heterotriangulene derivatives decorated with methoxycarbonyl- and methyl-sulfanyl-substituted dithiafulvenyl moieties. The association of these electron-rich compounds with fullerene C60 as electron acceptor was investigated by means of photophysical, voltammetric, and mass spectrometric methods and rationalized by DFT calculations. Importantly, light-induced interactions between the dithiafulvene-substituted N-heterotriangulene bearing methoxycarbonyl substituents with C60 leads to cooperative fluorescence. Quantitative Job plot analyses by means of fluorescence spectroscopy and voltammetry confirm a 1:1 association with binding constants in the order of 104 m−1. Supportive results for the supramolecular assembly of both N-heterotriangulenes with C60 were obtained by ESI mass spectrometric investigations in the gas phase.

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Enlightened association: Electron-rich N-heterotriangulenes featuring dithiafulvenyl moieties were synthesized and their association with C60 resulting in cooperative fluorescence was studied by photophysical, voltammetric, and mass spectrometric methods and rationalized by DFT calculations.

01 Jun 02:26

Odd [n]Cumulenes (n = 3, 5, 7, 9): Synthesis, Characterization, and Reactivity

by Dominik Wendinger and Rik R. Tykwinski

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.7b00164
24 May 02:03

Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C–C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides

Base‐Selective Five‐ versus Six‐Membered Ring Annulation in Palladium‐Catalyzed C–C Coupling Cascade Reactions: New Access to Electron‐Poor Polycyclic Aromatic Dicarboximides

Polycycles: Depending on the auxiliary bases applied in Pd-catalyzed C−C coupling reactions electron-poor polycyclic aromatic hydrocarbons are obtained by selective five- or six-membered ring annulation.

[Communication]
Sabine Seifert, David Schmidt, Kazutaka Shoyama, Frank Würthner
Angew. Chem. Int. Ed., May 23, 2017, https://doi.org/10.1002/anie.201702889 Read article

23 May 10:01

A Modular Flow Design for the meta-Selective C−H Arylation of Anilines

A Modular Flow Design for the meta‐Selective C−H Arylation of Anilines

One by one or all in one: meta-Arylated anilines are key moieties in a variety of high-value chemicals. To access these compounds, four key flow steps were identified, including synthesis of the diaryliodonium salt, meta-selective C−H arylation, and the removal of both the copper catalyst and the directing group. Each module has great individual potential, however, combining them allowed straightforward access to meta-arylated anilines within a reasonable time scale and with good purity.

[Communication]
Hannes P. L. Gemoets, Gabriele Laudadio, Kirsten Verstraete, Volker Hessel, Timothy Noël
Angew. Chem. Int. Ed., May 22, 2017, https://doi.org/10.1002/anie.201703369 Read article

23 May 09:55

Synthesis, Properties, and Semiconducting Characteristics of BF2 Complexes of β,β-Bisphenanthrene-Fused Azadipyrromethenes

by Wanle Sheng, Yu-Qing Zheng, Qinghua Wu, Yayang Wu, Changjiang Yu, Lijuan Jiao, Erhong Hao, Jie-Yu Wang and Jian Pei

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Organic Letters
DOI: 10.1021/acs.orglett.7b01133
20 May 04:24

Synthesis of a Three-Bladed Propeller-Shaped Triple [5]Helicene

by Hiromu Saito, Akira Uchida and Soichiro Watanabe

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00486
20 May 04:21

The first molecular dumbbell consisting of an endohedral Sc3N@C80 and an empty C60-fullerene building block

Chem. Commun., 2017, 53,7886-7889
DOI: 10.1039/C7CC03012F, Communication
Tao Wei, M. Eugenia Perez-Ojeda, Andreas Hirsch
Unprecedented synthesis of a fullerene dumbbell consisting of an endohedral metallic Sc3N@C80 and an empty C60 fullerene which reveals an exceptional electronic behaviour.
The content of this RSS Feed (c) The Royal Society of Chemistry
18 May 06:49

A Twisted Nanographene Consisting of 96 Carbon Atoms

A Twisted Nanographene Consisting of 96 Carbon Atoms

A new type of twisted nanographene containing an [8]circulene moiety in a polycyclic framework of 96 sp2 carbon atoms was synthesized from a macrocyclic diyne (see picture). Its structure was studied with X-ray crystallography and DFT calculations.

[Communication]
Kwan Yin Cheung, Chi Kit Chan, Zhifeng Liu, Qian Miao
Angew. Chem. Int. Ed., May 16, 2017, https://doi.org/10.1002/anie.201703754 Read article

18 May 06:48

meso-Cumulenic 2H-Corroles from meso-Ethynyl-3H-corroles

meso‐Cumulenic 2H‐Corroles from meso‐Ethynyl‐3H‐corroles

A π-conjugated dumbbell: [5]Cumulene-bridged 2H-corrole dimers capable of accommodating ZnII ions are synthesized from the corresponding meso-alkynyl-substituted 3H-corroles (see scheme). Their structures are revealed by X-ray diffraction analysis and the bond-length alternations in the cumulene segments are slightly larger than in conventional [n]cumulenes.

[Communication]
Kento Ueta, Koji Naoda, Shota Ooi, Takayuki Tanaka, Atsuhiro Osuka
Angew. Chem. Int. Ed., May 16, 2017, https://doi.org/10.1002/anie.201703139 Read article

18 May 06:46

Crystal-Packing-Driven Enrichment of Atropoisomers

Crystal‐Packing‐Driven Enrichment of Atropoisomers

Turn up the amplification: Solid-state heating of a mixture containing seven atropostereo-isomers converts almost all its components into a single product. This process takes place, even though the amplified stereoisomer represents only a minor (<25 mol %) component of the mixture at equilibrium in solution. Favorable crystal-packing interactions induce the high selectivity observed in this process.

[Communication]
Mona Sharafi, Joseph P. Campbell, Sinu C. Rajappan, Natavan Dudkina, Danielle L. Gray, Toby J. Woods, Jianing Li, Severin T. Schneebeli
Angew. Chem. Int. Ed., May 16, 2017, https://doi.org/10.1002/anie.201701876 Read article

17 May 03:57

Synthesis of Tetraaza[8]circulenes from Tetrathia[8]circulenes through an SNAr-Based Process

by Yuya Nagata, Shohei Kato, Yoshihiro Miyake and Hiroshi Shinokubo

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Organic Letters
DOI: 10.1021/acs.orglett.7b01074
27 Apr 20:07

Synthesis of Long Oxahelicenes by Polycyclization in a Flow Reactor

Synthesis of Long Oxahelicenes by Polycyclization in a Flow Reactor

Think big: Oxahelicenes comprising up to 19 fused rings (see example) were synthesized by multiple cobalt(I)-mediated cycloisomerization reactions of oligoynes, most efficiently in a flow reactor. The stereogenic centers in enantiomerically pure substrates steered the diastereoselective polycyclization of the oligoynes. Single-molecule conductivity was studied in a pyridooxa[9]helicene by the break-junction method.

[Communication]
Jindřich Nejedlý, Michal Šámal, Jiří Rybáček, Miroslava Tobrmanová, Florence Szydlo, Christophe Coudret, Maria Neumeier, Jaroslav Vacek, Jana Vacek Chocholoušová, Miloš Buděšínský, David Šaman, Lucie Bednárová, Ladislav Sieger, Irena G. Stará, Ivo Starý
Angew. Chem. Int. Ed., April 18, 2017, https://doi.org/10.1002/anie.201700341 Read article

27 Apr 10:50

C–H Functionalization of Azines

by Kei Murakami, Shuya Yamada, Takeshi Kaneda and Kenichiro Itami

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Chemical Reviews
DOI: 10.1021/acs.chemrev.7b00021
27 Apr 10:40

A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane

by Luuk Steemers, Martin J. Wanner, Andreas W. Ehlers, Henk Hiemstra and Jan H. van Maarseveen

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Organic Letters
DOI: 10.1021/acs.orglett.7b00877
25 Apr 13:45

Helical Nanoribbons for Ultra-Narrowband Photodetectors

by Yu Zhong, Thomas J. Sisto, Boyuan Zhang, Kiyoshi Miyata, X.-Y. Zhu, Michael L. Steigerwald, Fay Ng and Colin Nuckolls

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Journal of the American Chemical Society
DOI: 10.1021/jacs.6b13089
17 Apr 17:34

1,6- and 2,7-trans-β-Styryl Substituted Pyrenes Exhibiting Both Emissive and Semiconducting Properties in the Solid State

by Huajun Ju, Kang Wang, Jing Zhang, Hua Geng, Zitong Liu, Guanxin Zhang, Yongsheng Zhao and Deqing Zhang

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Chemistry of Materials
DOI: 10.1021/acs.chemmater.7b00056
17 Apr 17:32

Triphosphasumanene Trisulfide: High Out-of-Plane Anisotropy and Janus-Type π-Surfaces

by Shunsuke Furukawa, Yuki Suda, Junji Kobayashi, Takayuki Kawashima, Tomofumi Tada, Shintaro Fujii, Manabu Kiguchi and Masaichi Saito

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Journal of the American Chemical Society
DOI: 10.1021/jacs.6b12119
16 Apr 21:07

Entropy-Driven Ball-in-Bowl Assembly of Fullerene and Geodesic Phenylene Bowl

by Koki Ikemoto, Ryo Kobayashi, Sota Sato and Hiroyuki Isobe

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Organic Letters
DOI: 10.1021/acs.orglett.7b00899