Yamamoto Coupling for the Synthesis of Benzophenes and Acene-Based Cyclooctatetraenes

2018 ◽  
Vol 24 (39) ◽  
pp. 9919-9927 ◽  
Author(s):  
Elias C. Rüdiger ◽  
Silke Koser ◽  
Frank Rominger ◽  
Jan Freudenberg ◽  
Uwe H. F. Bunz
Keyword(s):  
Yamamoto Coupling

scholarly journals Bottom-up solution synthesis of narrow nitrogen-doped graphene nanoribbons

2014 ◽  
Vol 50 (32) ◽  
pp. 4172-4174 ◽  
Author(s):  
Timothy H. Vo ◽  
Mikhail Shekhirev ◽  
Donna A. Kunkel ◽  
François Orange ◽  
Maxime J.-F. Guinel ◽  
...  
Keyword(s):  
Graphene Nanoribbons ◽  
Solution Synthesis ◽  
Bottom Up ◽  
Molecular Precursors ◽  
Nitrogen Doped ◽  
Nitrogen Doped Graphene ◽  
Doped Graphene ◽  
Yamamoto Coupling

Large quantities of nitrogen-doped graphene nanoribbons can be synthesized via Yamamoto coupling of molecular precursors followed by cyclodehydrogenation using Scholl reaction.

scholarly journals Chiral Cyclic [n]Spirobifluorenylenes: Carbon Nanorings Consisting of Helically Arranged Quaterphenyl Rods Illustrating Partial Units of Woven Patterns

2020 ◽  
Author(s):  
Kaige Zhu, ◽  
Kosuke Kamochi ◽  
Takuya Kodama ◽  
Mamoru Tobisu ◽  
Toru Amaya
Keyword(s):  
Building Blocks ◽  
Spectroscopic Properties ◽  
Crystallographic Analysis ◽  
Quantum Yields ◽  
X Ray ◽  
New Family ◽  
Circularly Polarized Luminescence ◽  
Polarized Luminescence ◽  
Yamamoto Coupling ◽  
Carbon Nanorings

Chiral cyclic [n]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. The synthesis was accomplished by the Ni(0)-mediated Yamamoto-coupling of chiral spirobifluorene building blocks. The structures of the cyclic 3-, 4-, and 5-mers were determined by X-ray crystallographic analysis. These carbon nanorings exhibited a strong violet colored emission with high quantum yields in solution (95%, 93%, and 94% for 3-, 4-, and 5-mer, respectively). Other spectroscopic properties, including their chiroptical properties, were also investigated. The g-values for circularly polarized luminescence were found to be in the order of 10<sup>-3</sup>, where that of the 4-mer showed a relatively higher value 8.5 x 10<sup>-3</sup>. Characteristic spiroconjugation induced by multiple<br>3) bifluorenyl units, for example the even-odd effect of the number of units in the matching of the sign of the orbitals, were also indicated by DFT calculations.<br>

Accessing new microporous polyspirobifluorenes via a C/Si switch

2020 ◽  
Vol 56 (68) ◽  
pp. 9846-9849
Author(s):  
Andrei Nesmelov ◽  
David Lee ◽  
Christopher Bejger ◽  
Margaret Kocherga ◽  
Zachary Lyles ◽  
...  
Keyword(s):  
Microporous Materials ◽  
Easy Access ◽  
Yamamoto Coupling

A C/Si switch provides easy access to polybrominated spirosilabifluorenes with tailorable regioselectivities. Yamamoto coupling leads to fluorescent microporous materials that can act as a sensor for nitroaromatics.

Synthesis of a Contrapositionally Substituted Cyclohexa-meta-phenylene: A Ready-to-Use Precursor for Cyclohexa-meta-phenylene-Based Materials

Synlett ◽  
2019 ◽  
Vol 30 (16) ◽  
pp. 1886-1890
Author(s):  
Ifzan Arshad ◽  
Aamer Saeed ◽  
Pervaiz Ali Channar ◽  
Syeda Aaliya Shehzadi ◽  
Rana Muhammad Irfan
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Coupling Reactions ◽  
Iodine Monochloride ◽  
Synthetic Route ◽  
Metal Catalyzed ◽  
Yamamoto Coupling ◽  
Trimethylsilyl Groups

A contrapositionally substituted derivative of cyclohexa-meta-phenylene ([6]CMP) was synthesized by an intramolecular Yamamoto coupling reaction of an appropriate terphenyl unit containing a trimethylsilyl substituent. Iododesilylation of the trimethylsilyl groups of the product with iodine monochloride was used to incorporate iodo groups, an important functionality for metal-catalyzed coupling reactions. The iodo groups were also converted into a (pinacolato)boryl groups, another important functionality for coupling reactions. The diborylated [6]CMP is expected to be a versatile potential comonomer and a precursor for the synthesis of CMP-based materials. The synthetic route to the disubstituted [6]CMP included lithiation, Pd-catalyzed borylation, Suzuki coupling, and Yamamoto coupling. The structure of the product was established by NMR spectroscopy and mass spectrometry.

scholarly journals Starphenes and Phenes: Structures and Properties

2019 ◽  
Vol 01 (01) ◽  
pp. 001-018 ◽  
Author(s):  
Elias C. Rüdiger ◽  
Matthias Müller ◽  
Jan Freudenberg ◽  
Uwe H. F. Bunz
Keyword(s):  
Quantum Chemical ◽  
Synthetic Approach ◽  
Stille Coupling ◽  
Structures And Properties ◽  
Long Time ◽  
Yamamoto Coupling ◽  
Shotgun Approach ◽  
Insight Into

Acenes have been known for a long time but their larger congeners, starphenes and phenes, have only been recently accessible as processable and characterizable derivatives. In this personalized review, we delineate the synthetic approach developed by our group over the last four years. Nickel-mediated Yamamoto coupling of ortho-dibromoacenes generates cyclotrimers. If performed in a shotgun approach, i.e. with substituted 2,3-dibromotetracene or -pentacene in the presence of ortho-dibromobenzene or ortho-dibromoveratrole, trimeric phenes and tetramers would result. Cyclotrimers formed by a pentacenylene and two phenylenes are formally dibenzo[a,c]hexacenes. A direct way to obtain these species is to employ Stille coupling of a dimethylstannafluorene with 2,3-dibromoacenes. If tetrabromoanthracenes or tetrabromopentacenes are fed into this process, tetrabenzopentacene and tetrabenzoheptacenes are easily accessible. Optical and quantum-chemical characterizations provide insight into the electronic situation and aromaticity of these species.

scholarly journals Selective access to either a doubly boron-doped tetrabenzopentacene or an oxadiborepin from the same precursor

2019 ◽  
Vol 10 (39) ◽  
pp. 9017-9027 ◽  
Author(s):  
Julian Radtke ◽  
Kai Schickedanz ◽  
Marcel Bamberg ◽  
Luigi Menduti ◽  
Dieter Schollmeyer ◽  
...  
Keyword(s):  
Boron Doped ◽  
Yamamoto Coupling ◽  
Selective Access

Depending on the solvent, a brominated arylborane gave the multiple helicene B2-TBPA (pyridine) or the oxadiborepin ODBE (THF) after intramolecular Yamamoto coupling.

scholarly journals Ferrocene-Based Conjugated Microporous Polymers Derived from Yamamoto Coupling for Gas Storage and Dye Removal

Polymers ◽  
2020 ◽  
Vol 12 (3) ◽  
pp. 719 ◽  
Author(s):  
Zhiqiang Tan ◽  
Huimin Su ◽  
Yiwen Guo ◽  
Huan Liu ◽  
Bo Liao ◽  
...  
Keyword(s):  
Methyl Violet ◽  
Functional Materials ◽  
Gas Storage ◽  
Bet Surface Area ◽  
Energy And Environment ◽  
Microporous Polymers ◽  
Physicochemical Stability ◽  
High Efficient ◽  
Yamamoto Coupling ◽  
Conjugated Microporous Polymers

Conjugated microporous polymers (CMPs) have conjugated skeleton and permanent porosity, and exhibit huge potential in developing novel functional materials for resolving the challenging energy and environment issues. Metal-containing CMPs often exhibited unique properties. In the present manuscript, ferrocene-based conjugated microporous polymers (FcCMPs) were designed and synthesized with 1,1′-dibromoferrocene and 5,10,15,20-Tetrakis(4- bromophenyl) porphyrin (FcCMP-1) or Tetra (p-bromophenyl) methane (FcCMP-2) as building units via Yamamoto coupling. FcCMPs were amorphous, and exhibited excellent thermal and physicochemical stability. The BET surface area of FcCMP-1 and FcCMP-2 was 638 m2/g and 422 m2/g, respectively. In comparison with FcCMP-2, FcCMP-1 displayed better gas storage capacity due to higher porosity. FcCMPs were also used as an adsorbent for removal of methyl violet from aqueous solution, and exhibited excellent adsorption properties due to the interaction between electron-rich conjugated structure of the polymers and methyl violet with cationic groups. Moreover, FcCMPs could be extracted and regenerated by an eluent and then re-used for high efficient removal of methyl violet.

scholarly journals Preparation of substituted triphenylenes via nickel-mediated Yamamoto coupling

RSC Advances ◽  
2021 ◽  
Vol 11 (62) ◽  
pp. 39564-39569
Author(s):  
Zachary W. Schroeder ◽  
Joshua LeDrew ◽  
Vanessa M. Selmani ◽  
Kenneth E. Maly
Keyword(s):  
Efficient Synthesis ◽  
Discotic Mesogens ◽  
Yamamoto Coupling

Nickel-mediated Yamamoto coupling provides a concise and efficient synthesis of triphenylene derivatives, including electron-deficient discotic mesogens.

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