scholarly journals Towards triptycene functionalization and triptycene-linked porphyrin arrays

2020 ◽  
Vol 16 ◽  
pp. 763-777
Author(s):  
Gemma M Locke ◽  
Keith J Flanagan ◽  
Mathias O Senge
Keyword(s):  
Electron Transfer ◽  
Single Crystal ◽  
Cross Coupling ◽  
X Ray ◽  
Fluorescence Studies ◽  
Coupling Conditions ◽  
Porphyrin Dimer

Herein, 9,10-diethynyltriptycene is investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes, this work reports the first example of a linearly connected porphyrin dimer, linked through the bridgehead carbons of triptycene. Symmetric and unsymmetric examples of these complexes are demonstrated and single crystal X-ray analysis of an unsymmetrically substituted porphyrin dimer highlights the evident linearity in these systems. Moreover, initial UV–vis and fluorescence studies show the promise of triptycene as a linker for electron transfer studies, showcasing its isolating nature.

scholarly journals Towards Triptycene Functionalization and Triptycene-linked Porphyrin Arrays

2020 ◽  
Author(s):  
Gemma Locke ◽  
Keith Flanagan ◽  
Mathias Senge
Keyword(s):  
Electron Transfer ◽  
Single Crystal ◽  
Cross Coupling ◽  
X Ray ◽  
Fluorescence Studies ◽  
Coupling Conditions ◽  
Porphyrin Dimer

9,10-Diethynyltriptycene is investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes, this work reports the first example of a linearly connected porphyrin dimer, linked through the bridgehead carbons of triptycene. Symmetric and unsymmetric examples of these complexes are demonstrated and single crystal X-ray analysis of an unsymmetrically substituted porphyrin dimer highlights the evident linearity in these systems. Moreover, initial UV-Vis and fluorescence studies show the promise of triptycene as a linker for electron transfer studies, showcasing its isolating nature<br>

scholarly journals Towards Triptycene Functionalization and Triptycene-linked Porphyrin Arrays

2020 ◽  
Author(s):  
Gemma Locke ◽  
Keith Flanagan ◽  
Mathias Senge
Keyword(s):  
Electron Transfer ◽  
Single Crystal ◽  
Cross Coupling ◽  
X Ray ◽  
Fluorescence Studies ◽  
Coupling Conditions ◽  
Porphyrin Dimer

9,10-Diethynyltriptycene is investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes, this work reports the first example of a linearly connected porphyrin dimer, linked through the bridgehead carbons of triptycene. Symmetric and unsymmetric examples of these complexes are demonstrated and single crystal X-ray analysis of an unsymmetrically substituted porphyrin dimer highlights the evident linearity in these systems. Moreover, initial UV-Vis and fluorescence studies show the promise of triptycene as a linker for electron transfer studies, showcasing its isolating nature<br>

Chemical transformation of 1,2-oxazinochlorin derivatives: synthesis and X-ray crystal structure of a novel porphyrin-porphyrin dimer with a condensed cyclohexane ring

2007 ◽  
Vol 11 (01) ◽  
pp. 31-41 ◽  
Author(s):  
Yuliya V. Morozova ◽  
Dmitry V. Yashunsky ◽  
Zoya A. Starikova ◽  
Gelii V. Ponomarev
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Chemical Transformation ◽  
Trifluoroacetic Acid ◽  
Ring Opening ◽  
Nickel Complex ◽  
Cyclohexane Ring ◽  
X Ray ◽  
Reagent Treatment ◽  
Porphyrin Dimer

Base-assisted ring opening in 1,2-oxazinochlorin derivatives led selectively to the corresponding meso-cyanohydroxychlorin derivatives. The latter could then undergo acid-mediated carbocation formation followed by nucleophilic treatment to give different products, depending on the nature of the nucleophile reagent. Treatment of (E)- and/or (Z)-2-ethylidene-3-hydroxy-5-cyano-3,7,8,12,13,17,18-heptaethylchlorin nickel complex with a mixture of 5% trifluoroacetic acid and dichloromethane yielded a novel type porphyrin-porphyrin dimer with a condensed cyclohexane ring in an almost quantitative yield. The structure of this dimer was determined by single crystal X-ray analysis.

The Stereochemistry of Organometallic Compounds. LX. Rhodium-Catalyzed Reactions of Hydrogen and Carbon Monoxide With Alkenylanilines

1994 ◽  
Vol 47 (6) ◽  
pp. 1043 ◽  
Author(s):  
D Anastasiou ◽  
EM Campi ◽  
H Chaouk ◽  
GD Fallon ◽  
WR Jackson ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Carbon Monoxide ◽  
Single Crystal ◽  
Structure Determination ◽  
Cross Coupling ◽  
Organometallic Compounds ◽  
Single Crystal Structure ◽  
Crystal Structure Determination ◽  
X Ray ◽  
Catalyzed Reactions

Rhodium- catalysed reactions of o- or p- cyano-N-allylanilines with H2/CO give N- arylpyrrolidine aldehydes resulting from a double hydroformylation sequence. In contrast reactions of o- or p-methyl-N-allylanilines or N- allylaniline itself with H2/CO give ' dimeric ' compounds resulting from self-condensation reactions of an initially formed hydroformylation product together with varying amounts of the double hydroformylation product. Similar reactions of o-cyano-N-but-3-enylanilines give low yields of double hydroformylation products and major products arising from hydrogenation or cross coupling of intermediate enamines. The structure of one of these products, N-2-cyanophenyl-5-(N′-2-cyanophenyl-3-methyl-pyrrolidin-2-yl)-1,2,3,4-tetrahydropyridine (17) (IUPAC name: 2-[5-{1-(2-cyanophenyl)-3-methylpyrrolidin-2-yl}-1,2,3,4-tetrahydropyridin-1-yl] benzonitrile ) was confirmed by an X-ray single-crystal structure determination.

Covalent Analogues of DNA Base-Pairs and Triplets V. Synthesis of Purine-Purine and Purine-Pyrimidine Conjugates Connected by Diverse Types of Acyclic Carbon Linkages

2002 ◽  
Vol 67 (10) ◽  
pp. 1560-1578 ◽  
Author(s):  
Michal Hocek ◽  
Hana Dvořáková ◽  
Ivana Císařová
Keyword(s):  
Single Crystal ◽  
Crystal Structures ◽  
Base Pair ◽  
Cross Coupling ◽  
X Ray Diffraction ◽  
Base Pairs ◽  
X Ray ◽  
Dna Base ◽  
Dna Base Pairs ◽  
Purine Pyrimidine

The title 1,2-bis(purin-6-yl)acetylenes, -diacetylenes, -ethylenes and -ethanes were prepared as covalent base-pair analogues starting from 6-ethynylpurines and 6-iodopurines by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by hydrogenations. 6-[(1,3-Dimethyluracil-5-yl)ethynyl]purine (11) was prepared analogously and hydrogenated to the corresponding purine-pyrimidine conjugates linked via vinylene and ethylene linkers. Unlike the cytostatic bis(purin-6-yl)acetylenes and -diacetylenes, the purine-pyrimidine conjugates were inactive. Crystal structures of bis(purin-6-yl)acetylene 6a, -diacetylene 8a and -ethane 5a were determined by single-crystal X-ray diffraction.

Investigation of the light-induced electron-transfer-coupled spin transition in a cyanide-bridged [Co2Fe2] complex by X-ray diffraction and absorption measurements

2014 ◽  
Vol 1 (7) ◽  
pp. 540-543 ◽  
Author(s):  
Yoshihiro Sekine ◽  
Masayuki Nihei ◽  
Reiji Kumai ◽  
Hironori Nakao ◽  
Youichi Murakami ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Crystal ◽  
Spin Transition ◽  
X Ray Diffraction ◽  
Tetranuclear Complex ◽  
X Ray ◽  
Absorption Measurements

The light-induced electron-transfer-coupled spin transition in a cyanide-bridged [Co2Fe2] tetranuclear complex has been investigated by single-crystal X-ray diffraction and absorption measurements.

Synthesis and studies of covalently linked BF2-oxasmaragdyrin-BODIPY and BF2-oxasmaragdyrin-ferrocene dyads

2013 ◽  
Vol 17 (01n02) ◽  
pp. 157-164 ◽  
Author(s):  
Yogita Pareek ◽  
Mangalampalli Ravikanth
Keyword(s):  
Electron Transfer ◽  
Energy Transfer ◽  
Excited State ◽  
Photoinduced Electron Transfer ◽  
Individual Characteristic ◽  
Electrochemical Studies ◽  
Fluorescence Studies ◽  
Coupling Conditions ◽  
Characteristic Features ◽  
Covalently Linked

Covalently linked BF2 -oxasmaragdyrin-BODIPY and BF2 -oxasmaragdyrin-ferrocene dyads were synthesized by coupling of meso-triaryl oxasmaragdyrin containing meso-iodophenyl group with meso-(p-ethynylphenyl) borondipyrromethene and α-ethynyl ferrocene respectively under mild Pd(0) coupling conditions. NMR, absorption and electrochemical studies indicated that the two moieties in the dyads retain their individual characteristic features. The fluorescence studies indicated a possibility of photoinduced singlet-singlet energy transfer from BODIPY unit to BF2 -oxasmaragdyrin unit in BF2 -oxasmaragdyrin-BODIPY dyad and photoinduced electron transfer from ferrocene unit to excited state of BF2 -oxasmaragdyrin unit in BF2 -oxasmaragdyrin-ferrocene dyad.

One-Pot Synthesis of a Cyclic Pyrene Octamer from Two Bifunctionalized Pyrene Monomers

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 344-347
Author(s):  
Hiroko Yamada ◽  
Naoki Aratani ◽  
Peifeng Mei ◽  
Ryo Kurosaki ◽  
Akinobu Matsumoto
Keyword(s):  
Molecular Structure ◽  
Single Crystal ◽  
Diffraction Analysis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis ◽  
Cross Coupling Reaction

AbstractA 2,2′-tert-butyl-5,9-6′,8′-cyclooctameric pyrenylene ([8]CP) was synthesized by a one-pot Suzuki–Miyaura cross-coupling reaction from two kinds of bifunctionalized monomers, as a rare example of a cyclic octamer. The octameric molecular structure of [8]CP was revealed by single-crystal X-ray diffraction analysis.

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