In chemistry, vinylene (also ethenylene or 1,2-ethenediyl)[1] is a divalent functional group (a part of a molecule)[2] with formula −CH=CH−;[3] namely, two carbons, each connected to the other by a double bond, to an hydrogen atom by a single bond, and to the rest of the molecule by another single bond.[4][5]
This group can be viewed as a molecule of ethene (ethylene, H2C=CH2) with an hydrogen removed from each carbon; or a vinyl group −CH=CH2 with one hydrogen removed from the terminal carbon.[6][7][8] It should not be confused with the vinylidene group =C=CH2 or >C=CH2.
A vinylene unit attached to two distinct atoms other than hydrogen (namely R−CH=CH−R') is a source of cis-trans isomerism.[9][10]
The vinylene group is the repeating unit in polyacetylene and in polyenes.[11]
^Liu, Qibo; Burton, Donald J. (2002-05-02). "Stereoselective preparation of (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] and stereospecific synthesis of (E)-1,2-difluorostilbenes". Organic Letters. 4 (9): 1483–1485. doi:10.1021/ol025686+. ISSN 1523-7060. PMID 11975609.
^Blockhuys, null; Claes, null; Van Grieken R, null; Geise, null (2000-07-15). "Assessing the molecular weight of a conducting polymer by grazing emission XRF". Analytical Chemistry. 72 (14): 3366–3368. doi:10.1021/ac990877k. ISSN 1520-6882. PMID 10939413.
^Sasidharan, Manickam; Bhaumik, Asim (2013-04-10). "Novel and mild synthetic strategy for the sulfonic Acid functionalization in periodic mesoporous ethenylene-silica". ACS Applied Materials & Interfaces. 5 (7): 2618–2625. doi:10.1021/am4000326. ISSN 1944-8252. PMID 23484521.
^Reichert, Edward. "Ethylene bichloride as an anæsthetic agent: with a consideration of ethylene methylethylate, ethylene ethylate, ethyl nitrate, and ethylidene bichloride". National Library of Medicine. Retrieved 2022-09-28.
^"Chemical warfare agents and related chemical problems". National Library of Medicine. 14111270RX1. 1946. Retrieved 2022-09-28.
^Mukherjee, Soumya (2019-01-01). "Recent advancements in the mechanism of nitric oxide signaling associated with hydrogen sulfide and melatonin crosstalk during ethylene-induced fruit ripening in plants". Nitric Oxide: Biology and Chemistry. 82: 25–34. doi:10.1016/j.niox.2018.11.003. ISSN 1089-8611. PMID 30465876. S2CID 53753053.
^Valentini, Alessio; Rivero, Daniel; Zapata, Felipe; García-Iriepa, Cristina; Marazzi, Marco; Palmeiro, Raúl; Fdez Galván, Ignacio; Sampedro, Diego; Olivucci, Massimo; Frutos, Luis Manuel (2017-03-27). "Optomechanical Control of Quantum Yield in Trans-Cis Ultrafast Photoisomerization of a Retinal Chromophore Model". Angewandte Chemie International Edition. 56 (14): 3842–3846. doi:10.1002/anie.201611265. ISSN 1521-3773. PMID 28251753.
^Georgiev, Anton; Kostadinov, Anton; Ivanov, Deyan; Dimov, Deyan; Stoyanov, Simeon; Nedelchev, Lian; Nazarova, Dimana; Yancheva, Denitsa (2018-03-01). "Synthesis, spectroscopic and TD-DFT quantum mechanical study of azo-azomethine dyes. A laser induced trans-cis-trans photoisomerization cycle". Spectrochimica Acta Part A: Molecular Spectroscopy. 192: 263–274. Bibcode:2018AcSpA.192..263G. doi:10.1016/j.saa.2017.11.016. PMID 29156313.
^Johnston, Dean H.; Gao, Lei; Lonergan, Mark C. (2010-03-23). "Kinetic Study of the Ring-Opening Metathesis Copolymerization of Ionic with Nonionic Cyclooctatetraene Derivatives To Yield Polyacetylene Ionomers". Macromolecules. 43 (6): 2676–2683. Bibcode:2010MaMol..43.2676J. doi:10.1021/ma100034h. ISSN 0024-9297.
In chemistry, vinylene (also ethenylene or 1,2-ethenediyl) is a divalent functional group (a part of a molecule) with formula −CH=CH−; namely, two carbons...
species ethenylidenes have the connectivity =C=CH2. Vinylenegroup, −CH=CH− Methylene group, −CH2− Vinyl group, −CH=CH2 Barry M. Trost; Andrew McClory "Metal...
copolymers are the main class of conductive polymers. Poly(p-phenylene vinylene) (PPV) and its soluble derivatives have emerged as the prototypical electroluminescent...
related aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen, or sulfur. Examples...
unsubstituted poly(p-phenylene vinylene) (PPV) is typically insoluble, a number of PPVs and related poly(naphthalene vinylene)s (PNVs) that are soluble in...
polymeric semi-conductor LED's (Light Emitting Diodes), based on polyphenylene-vinylene. Friend lives in Cambridge with his wife, Carol Anne Maxwell (née Beales)...
the nanoscale has been modified, and nanostructures of poly(p-phenylene vinylene) (an electroluminescence conjugated polymer) have been created. Nanoscale...
processible conjugated polymers poly(P-phenylene vinylene) and poly(4,4'-diphenylene diphenyl vinylene). jisc.ac.uk (PhD thesis). University of Cambridge...
2]paracyclophane-1,9-diene has been applied in ROMP to a poly(p-phenylene vinylene) with alternating cis-alkene and trans-alkene bonds using Grubbs' second...
bullvalene molecule is a cyclopropane platform with three vinylene arms conjoined at a methine group. This arrangement enables a degenerate Cope rearrangement...
polyacetylene, polypyrrole, polythiophenes, and polyaniline. Poly(p-phenylene vinylene) and its derivatives are electroluminescent semiconducting polymers....
M. Vaeth & K. F. Jensen (1999). "Selective growth of poly(p-phenylene vinylene) prepared by chemical vapor deposition". Advanced Materials. 11 (10): 814–820...
light-emitting diodes based on poly ( m -phenylene vinylene-co-2, 5-dioctoxy- p -phenylene vinylene)". Applied Physics Letters. 77 (9): 1393–1395. Bibcode:2000ApPhL...
tacticity, copolymer distribution, the degree of branching, by its end-groups, crosslinks, crystallinity and thermal properties such as its glass transition...
is used in the synthesis of the phosphorus pendant of Poly(p-phenylene vinylene): . The reduction or oxidation of phosphaalynes can produce radical phosphorus...
100 nm) of organic semiconductors including polymers, such as polyphenylene vinylene and small-molecule compounds like copper phthalocyanine (a blue or green...
4-diyl)-dithiophene]-5,5′-diyl-alt-vinylene) conjugated polymer for PA-guided PTT with PCE 71% (@ 808 nm, 0.3 W cm−2). The vinylene bonds in the main chain improves...
highlighted the development of a soluble derivative of poly(phenylene‐vinylene), and buckminsterfullerene, C60. His research also revealed the fact that...
amphiphilic gold nanoparticles decorated with a mixed shell of oligo(p-phenylene vinylene)s and ethyleneoxide ligands". Journal of Materials Chemistry. 18 (29):...
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