Shared posts

30 Nov 15:28

Spiro-BODIPYs with a Diaryl Chelate: Impact on Aggregation and Luminescence

by Kang Yuan, Xiang Wang, Soren K Mellerup, Igor Kozin and Suning Wang

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b02602
27 Nov 11:47

Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60

Chem. Sci., 2018, 9,819-824
DOI: 10.1039/C7SC04453D, Edge Article
Open Access Open Access
Hiroki Yokoi, Satoru Hiroto, Daisuke Sakamaki, Shu Seki, Hiroshi Shinokubo
A directly connected azabuckybowl dimer forms a 1 : 1 complex with C60 in a diluted solution, while 1D chain supramolecular assemblies are obtained upon increasing the concentration.
The content of this RSS Feed (c) The Royal Society of Chemistry
22 Nov 12:09

Fluorous photosensitizers enhance photodynamic therapy with perfluorocarbon nanoemulsions

Chem. Commun., 2017, 53,13043-13046
DOI: 10.1039/C7CC07038A, Communication
Rachael A. Day, Daniel A. Estabrook, Jessica K. Logan, Ellen M. Sletten
Photodynamic therapy (PDT) requires a photosensitizer, light and oxygen to induce cell death. Here, we simultaneously deliver oxygen and photosensitizer using perfluorocarbon nanoemulsions.
The content of this RSS Feed (c) The Royal Society of Chemistry
21 Nov 14:32

D–π–A–π–D Dyes with a 1,3,2-Dioxaborine Cycle in the Polymethine Chain: Efficient Long-Wavelength Fluorophores

by Vladyslav Polishchuk, Mariia Stanko, Andrii V Kulinich, Mykola Shandura

The nitrile group in newly synthesized 5-cyano-2,2-difluoro-4,6-dimethyl-1,3,2-dioxaborine is shown to significantly increase the acidity of the methyl groups. This allows the cyanine condensation with both methyl groups to form D–π–A–π–D dyes in which the dioxaborine cycle is a part of the polymethine chain. There, the reactivity of the remaining methyl group in the semi-product is reduced enough to perform the reaction stepwise, giving access to nonsymmetric derivatives. The synthesis of dyes with various electron donor termini [indole, benzothiazole, pyran, 4-(dialkylamino)phenyl] and with different polymethine chain lengths is reported. The obtained compounds show intense absorption and fluorescence in the red and NIR region, their fluorescence brightness (the product of the molar extinction and the fluorescence quantum yield) attaining a value of 200,000 m–1 cm–1. They are characterized by small-scale positive solvatochromism, yet their fluorescence quantum yield is much more sensitive to ambient polarity. Time-dependent (TD)DFT calculations have been performed to study the electronic structure of the new dioxaborines and reveal the nature of the long-wavelength electronic transitions in those molecules.

Thumbnail image of graphical abstract

A newly synthesized 1,3,2-dioxaborine synthon comprises a 5-cyano group which significantly increases its activity in cyanine condensations. It gives access to new D–π–A–π–D functional compounds. These dyes intensely absorb and emit in the red and NIR region, their fluorescence quantum yield increasing in step with the electron-donating ability of the terminal groups.

15 Nov 13:44

DNA-Decorated Two-Dimensional Crystalline Nanosheets

by Shine K. Albert, Irla Sivakumar, Murali Golla, Hari Veera Prasad Thelu, Nithiyanandan Krishnan, Joseph Libin K. L., Ashish and Reji Varghese

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b09283
15 Nov 13:44

Thiadiazoloquinoxaline-Fused Naphthalenediimides for n-Type Organic Field-Effect Transistors (OFETs)

by Ben-Lin Hu, Ke Zhang, Cunbin An, Wojciech Pisula and Martin Baumgarten

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.7b03041
14 Nov 09:29

Synthesis of Pyrrole-Fused Corannulenes: 1,3-Dipolar Cycloaddition of Azomethine Ylides to Corannulene

Synthesis of Pyrrole‐Fused Corannulenes: 1,3‐Dipolar Cycloaddition of Azomethine Ylides to Corannulene

Along the rim: Reported is the 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide to corannulene, a reaction which occurs exclusively at the rim bond of corannulene, from the convex side in an exo fashion. The cycloadducts were converted, by oxidative dehydrogenation, into pyrrole-fused corannulenes, which exhibited pronounced solvatofluorochromism.

[Communication]
Yuki Tokimaru, Shingo Ito, Kyoko Nozaki
Angew. Chem. Int. Ed., November 13, 2017, https://doi.org/10.1002/anie.201707087 Read article

10 Nov 11:38

Edge Functionalization of Structurally Defined Graphene Nanoribbons for Modulating the Self-Assembled Structures

by Ashok Keerthi, Boya Radha, Daniele Rizzo, Hao Lu, Valentin Diez Cabanes, Ian Cheng-Yi Hou, David Beljonne, Jérôme Cornil, Cinzia Casiraghi, Martin Baumgarten, Klaus Müllen and Akimitsu Narita

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b09031
28 Oct 12:22

Diferrocenes Bridged by a Geminal Diethynylethene Scaffold with Varying Pendant Substituents: Electronic Interactions in Cross-Conjugated System

by Yang Fan, Hua-Min Li, Guo-Dong Zou, Xu Zhang, Ying-Le Pan, Ke-Ke Cao, Meng-Li Zhang, Pei-Lin Ma and Hai-Ting Lu

TOC Graphic

Organometallics
DOI: 10.1021/acs.organomet.7b00686
27 Oct 11:42

Exploring the Formation of Black Phosphorus Intercalation Compounds with Alkali Metals

Exploring the Formation of Black Phosphorus Intercalation Compounds with Alkali Metals

Black to the future: The bulk intercalation of black phosphorus with alkali metals (namely: K and Na; black spheres) has been developed, showing a complex dynamic structural behavior. By in situ Raman spectroscopy and DFT calculations straightforward fingerprints for the identification of black phosphorus intercalation compounds (BPICs) have been demonstrated.

[Communication]
Gonzalo Abellán, Christian Neiss, Vicent Lloret, Stefan Wild, Julio C. Chacón-Torres, Katharina Werbach, Filippo Fedi, Hidetsugu Shiozawa, Andreas Görling, Herwig Peterlik, Thomas Pichler, Frank Hauke, Andreas Hirsch
Angew. Chem. Int. Ed., October 26, 2017, https://doi.org/10.1002/anie.201707462 Read article

27 Oct 11:41

Flash Vacuum Pyrolysis: Techniques and Reactions

Flash Vacuum Pyrolysis: Techniques and Reactions

Quick as a flash: This review describes flash pyrolysis methods for the synthesis of unusual molecules and for the characterization of reactive intermediates. The most important methods are presented, and an overview of typical reactions and observations that are possible with the various techniques are presented.

[Review]
Curt Wentrup
Angew. Chem. Int. Ed., October 25, 2017, https://doi.org/10.1002/anie.201705118 Read article

21 Oct 10:08

Regioselective Synthesis of [3]Naphthylenes and Tuning of Their Antiaromaticity

by Zexin Jin, Yew Chin Teo, Simon J. Teat and Yan Xia

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b09222
21 Oct 10:07

Red Light-Triggered CO Release from Mn2(CO)10 Using Triplet Sensitization in Polymer Nonwoven Fabrics

by Sven H. C. Askes, G. Upendar Reddy, Ralf Wyrwa, Sylvestre Bonnet and Alexander Schiller

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b07427
06 Oct 08:23

Supramolecular chemotherapy based on host-guest molecular recognition: a novel strategy in the battle against cancer with a bright future

Chem. Soc. Rev., 2017, 46,7021-7053
DOI: 10.1039/C6CS00898D, Review Article
Jiong Zhou, Guocan Yu, Feihe Huang
This review highlights the progress of supramolecular chemotherapy in cancer treatment based on host-guest interactions and provides guidance on the design of new targeting supramolecular chemotherapy combining diagnostic and therapeutic functions.
The content of this RSS Feed (c) The Royal Society of Chemistry
29 Sep 07:40

Direct Synthesis of Large-Scale Ortho-Iodinated Perylene Diimides: Key Precursors for Functional Dyes

by Jiajun Wu, Dezhi He, Li Zhang, Yudong Liu, Xiaogang Mo, Jianbin Lin and Hui-jun Zhang

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.7b02718
28 Sep 16:00

Long-Range Orientational Self-Assembly, Spatially Controlled Deprotonation, and Off-Centered Metalation of an Expanded Porphyrin

by Borja Cirera, Olga Trukhina, Jonas Björk, Giovanni Bottari, Jonathan Rodríguez-Fernández, Alberto Martin-Jimenez, Mikhail K. Islyaikin, Roberto Otero, José M. Gallego, Rodolfo Miranda, Tomás Torres and David Ecija

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b06406
20 Sep 08:20

4,5,9,10-Pyrene Diimides: A Family of Aromatic Diimides Exhibiting High Electron Mobility and Two-Photon Excited Emission

4,5,9,10‐Pyrene Diimides: A Family of Aromatic Diimides Exhibiting High Electron Mobility and Two‐Photon Excited Emission

Conductive and emissive: Facile synthetic routes to reach the K-region of pyrene and produce 4,5,9,10-pyrene diimide (PyDI) derivatives are reported. The PyDI derivatives exhibited efficient electron transport properties, with the highest electron mobility of up to 3.08 cm2 V−1 s−1. The tert-butyl-substituted compounds (t-PyDI) also showed good one- and two-photon excited fluorescence properties.

[Communication]
Ze-Hua Wu, Zhuo-Ting Huang, Rui-Xue Guo, Chun-Lin Sun, Li-Chuan Chen, Bing Sun, Zi-Fa Shi, Xiangfeng Shao, Hanying Li, Hao-Li Zhang
Angew. Chem. Int. Ed., September 18, 2017, https://doi.org/10.1002/anie.201707529 Read article

14 Sep 08:50

Electron-Poor Bowl-Shaped Polycyclic Aromatic Dicarboximides: Synthesis, Crystal Structures, and Optical and Redox Properties

by Kazutaka Shoyama, David Schmidt, Magnus Mahl and Frank Würthner

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.7b02618
13 Sep 07:53

Synthesis of Phenalenyl-Fused Pyrylium Cations: Divergent C−H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes

Synthesis of Phenalenyl‐Fused Pyrylium Cations: Divergent C−H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes

Shell out: The rhodium-catalyzed C−H activation/annulation sequence of naphthalene-type aldehydes with internal alkynes has been developed to provide access to phenalenyl-fused pyrylium cations. Also disclosed is the open-shell radical character of the reduced products.

[Communication]
Jiangliang Yin, Meiling Tan, Di Wu, Ruyong Jiang, Chengming Li, Jingsong You
Angew. Chem. Int. Ed., September 11, 2017, https://doi.org/10.1002/anie.201708127 Read article

13 Sep 07:52

Luminescent Carbon Dot Mimics Assembled on DNA

by Ke Min Chan, Wang Xu, Hyukin Kwon, Anna M. Kietrys and Eric T. Kool

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b07420
01 Sep 11:25

From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom

From Fenestrindane towards Saddle‐Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom

Warped nanographene: Two fourfold bay-bridged fenestrindane derivatives were prepared in good yields through a non-classical Scholl-type cyclization, paving the way to saddle-shaped nanographenes.

[Communication]
Wai-Shing Wong, Chun-Fai Ng, Dietmar Kuck, Hak-Fun Chow
Angew. Chem. Int. Ed., August 29, 2017, https://doi.org/10.1002/anie.201707505 Read article

31 Aug 15:40

The Rolling-Up of Oligophenylenes to Nanographenes by a HF-Zipping Approach

by Ann-Kristin Steiner, Konstantin Y Amsharov

Abstract

Intramolecular aryl–aryl coupling is the key transformation in the rational synthesis of nanographenes and nanoribbons. In this respect the C−F bond activation was shown to be a versatile alternative enabling the synthesis of several unique carbon-based nanostructures. Herein we describe an unprecedentedly challenging transformation showing that the C−F bond activation by aluminum oxide allows highly effective domino-like C−C bond formation. Despite the flexible nature of oligophenylene-based precursors efficient regioselective zipping to the target nanostructures was achieved. We show that fluorine positions in the precursor structure unambiguously dictate the “running of the zipping-program” which results in rolling-up of linear oligophenylene chains around phenyl moieties yielding target nanographenes. The high efficiency of zipping makes this approach attractive for the synthesis of unsubstituted nanographenes which are difficult to obtain in pure form by other methods.

Thumbnail image of graphical abstract

Roll up, roll up: Virtually linear fluorinated oligophenylenes are converted into the “preprogrammed” challenging nanographenes via effective domino-like aryl–aryl coupling. The fluorine positions in the precursor structure unambiguously dictate the running of the “HF-zipping-program” leading to the formation of the target nanographene structure.

24 Aug 16:29

Porphyrin Antennas on Carbon Nanodots: Excited State Energy and Electron Transduction

Porphyrin Antennas on Carbon Nanodots: Excited State Energy and Electron Transduction

Antennas up! The synthesis and electron donor–acceptor features of a novel hybrid nanomaterial are reported. The nanohybrid combines the light-harvesting and electron-donating properties of a meso-tetraarylporphyrin (TArP) with the electron-accepting features of nitrogen-doped carbon nanodots (NCNDs).

[Communication]
Francesca Arcudi, Volker Strauss, Luka Đorđević, Alejandro Cadranel, Dirk M. Guldi, Maurizio Prato
Angew. Chem. Int. Ed., August 24, 2017, https://doi.org/10.1002/anie.201704544 Read article

24 Aug 16:28

Tetraalkoxyphenanthrene-Fused Hexadecadehydro[20]- and Tetracosadehydro[30]annulenes: Syntheses, Aromaticity/Antiaromaticity, Electronic Properties, and Self-Assembly

by Nobutaka Takahashi, Shin-ichiro Kato, Minoru Yamaji, Masahiko Ueno, Ryunosuke Iwabuchi, Yui Shimizu, Masashi Nitani, Yutaka Ie, Yoshio Aso, Takeshi Yamanobe, Hiroki Uehara and Yosuke Nakamura

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b01165
24 Aug 08:33

A meso–meso β-β β-β Triply Linked Subporphyrin Dimer

A meso–meso β‐β β‐β Triply Linked Subporphyrin Dimer

A triply linked subporphyrin dimer was synthesized by stepwise reductive elimination of a β-to-β doubly PtII-bridged subporphyrin dimer with the concurrent formation of the meso–meso bond. Despite the curved structure, the triply linked dimer displayed a remarkably red-shifted absorption spectrum and narrow electrochemical HOMO–LUMO gap because of the effectively conjugated π-electronic network.

[Communication]
Yasuhiro Okuda, Norihito Fukui, Jinseok Kim, Taeyeon Kim, Hua-Wei Jiang, Graeme Copley, Masaaki Kitano, Dongho Kim, Atsuhiro Osuka
Angew. Chem. Int. Ed., August 23, 2017, https://doi.org/10.1002/anie.201707123 Read article

24 Aug 08:31

Synthesis of Silicon and Germanium-Containing Heterosumanenes via Rhodium-Catalyzed Cyclodehydrogenation of Silicon/Germanium–Hydrogen and Carbon–Hydrogen Bonds

by Dandan Zhou, Ya Gao, Bingxin Liu, Qitao Tan and Bin Xu

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.7b02254
22 Aug 07:27

Direct Covalent Coupling of Porphyrins to Graphene

by Daniela Dasler, Ricarda A. Schäfer, Martin B. Minameyer, Jakob F. Hitzenberger, Frank Hauke, Thomas Drewello and Andreas Hirsch

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b04122
18 Aug 08:40

Metal-Free Oxidative C–C Coupling of Arylamines Using a Quinone-Based Organic Oxidant

by Sudhakar Maddala, Sudesh Mallick and Parthasarathy Venkatakrishnan

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b01377
17 Aug 07:40

Highly Efficient Chemiluminescence Probe for the Detection of Singlet Oxygen in Living Cells

Highly Efficient Chemiluminescence Probe for the Detection of Singlet Oxygen in Living Cells

Illuminating singlet oxygen: A chemiluminescence probe for singlet oxygen based on dioxetane formation is described. The dioxetane decomposes by a highly efficient chemiexcitation process to emit green light. The probe was used to detect and image intracellular 1O2 produced by a photosensitizer in HeLa cells during photodynamic therapy.

[Communication]
Nir Hananya, Ori Green, Rachel Blau, Ronit Satchi-Fainaro, Doron Shabat
Angew. Chem. Int. Ed., August 16, 2017, https://doi.org/10.1002/anie.201705803 Read article

16 Aug 07:54

Bodipy–Anthracene Dyads as Triplet Photosensitizers: Effect of Chromophore Orientation on Triplet-State Formation Efficiency and Application in Triplet–Triplet Annihilation Upconversion

by Zhijia Wang and Jianzhang Zhao

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.7b02047