Search for "π-conjugated" in Full Text gives 108 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225
Graphical Abstract
Figure 1: Loschmidt’s structure proposal for benzene (1) (Scheme 181 from [3]) and the corresponding modern stru...
Figure 2: The first isolated bisallenes.
Figure 3: Carbon skeletons of selected bisallenes discussed in this review.
Scheme 1: The preparation of 1,2,4,5-hexatetraene (2).
Scheme 2: The preparation of a conjugated bisallene by the DMS-protocol.
Scheme 3: Preparation of the 3-deuterio- and 3,4-dideuterio derivatives of 24.
Scheme 4: A versatile method to prepare alkylated conjugated bisallenes and other allenes.
Scheme 5: A preparation of 3,4-dimethyl-1,2,4,5-hexatetraene (38).
Scheme 6: A (C6 + 0)-approach to 1,2,4,5-hexatetraene (2).
Scheme 7: The preparation of a fully alkylated bisallenes from a 2,4-hexadiyne-1,6-diol diacetate.
Scheme 8: The preparation of the first phenyl-substituted conjugated bisallenes 3 and 4.
Scheme 9: Selective hydrogenation of [5]cumulenes to conjugated bisallenes: another (C6 + 0)-route.
Scheme 10: Aryl-substituted conjugated bisallenes by a (C3 + C3)-approach.
Scheme 11: Hexaphenyl-1,2,4,5-hexatetraene (59) by a (C3 + C3)-approach.
Scheme 12: An allenation route to conjugated bisallenes.
Scheme 13: The preparation of 3,4-difunctionalized conjugated bisallenes.
Scheme 14: Problems during the preparation of sulfur-substituted conjugated bisallenes.
Scheme 15: The preparation of 3,4-dibromo bisallenes.
Scheme 16: Generation of allenolates by an oxy-Cope rearrangement.
Scheme 17: A linear trimerization of alkynes to conjugated bisallenes: a (C2 + C2 + C2)-protocol.
Scheme 18: Preparation of a TMS-substituted conjugated bisallene by a C3-dimerization route.
Scheme 19: A bis(trimethylsilyl)bisallene by a C3-coupling protocol.
Scheme 20: The rearrangement of highly substituted benzene derivatives into their conjugated bisallenic isomer...
Scheme 21: From fully substituted benzene derivatives to fully substituted bisallenes.
Scheme 22: From a bicyclopropenyl to a conjugated bisallene derivative.
Scheme 23: The conversion of a bismethylenecyclobutene into a conjugated bisallene.
Scheme 24: The preparation of monofunctionalized bisallenes.
Scheme 25: Preparation of bisallene diols and their cyclization to dihydrofurans.
Scheme 26: A 3,4-difunctionalized conjugated bisallene by a C3-coupling process.
Scheme 27: Preparation of a bisallenic diketone by a coupling reaction.
Scheme 28: Sulfur and selenium-substituted bisallenes by a [2.3]sigmatropic rearrangement.
Scheme 29: The biallenylation of azetidinones.
Scheme 30: The preparation of a fully ferrocenylated conjugated bisallene.
Scheme 31: The first isomerization of a 1,5-hexadiyne to a 1,2,4,5-hexatetraene.
Scheme 32: The preparation of alkynyl-substituted bisallenes by a C3-dimerization protocol.
Scheme 33: Preparation of another completely ferrocenylated bisallene.
Scheme 34: The cyclization of 1,5-hexadiyne (129) to 3,4-bismethylenecyclobutene (130) via 1,2,4,5-hexatetraen...
Scheme 35: Stereochemistry of the thermal cyclization of bisallenes to bismethylenecyclobutenes.
Scheme 36: Bisallene→bismethylenecyclobutene ring closures in the solid state.
Scheme 37: A bisallene cyclization/dimerization reaction.
Scheme 38: A selection of Diels–Alder additions of 1,2,4,5-hexatetraene with various double-bond dienophiles.
Scheme 39: The stereochemistry of the [2 + 4] cycloaddition to conjugated bisallenes.
Scheme 40: Preparation of azetidinone derivatives from conjugated bisallenes.
Scheme 41: Cycloaddition of heterodienophiles to a conjugated bisallene.
Scheme 42: Addition of triple-bond dienophiles to conjugated bisallenes.
Scheme 43: Sulfur dioxide addition to conjugated bisallenes.
Scheme 44: The addition of a germylene to a conjugated bisallene.
Scheme 45: Trapping of conjugated bisallenes with phosphinidenes.
Scheme 46: The cyclopropanantion of 1,2,4,5-hexatetraene (2).
Scheme 47: Photochemical reactions involving conjugated bisallenes.
Scheme 48: Base-catalyzed isomerizations of conjugated bisallenes.
Scheme 49: Ionic additions to a conjugated bisallene.
Scheme 50: Oxidation reactions of a conjugated bisallene.
Scheme 51: The mechanism of oxidation of the bisallene 24.
Scheme 52: CuCl-catalyzed cyclization of 1,2,4,5-hexatetraene (2).
Scheme 53: The conversion of conjugated bisallenes into cyclopentenones.
Scheme 54: Oligomerization of a conjugated bisallene by nickel catalysts.
Scheme 55: Generation of 1,2,5,6-heptatetraene (229) as a reaction intermediate.
Scheme 56: The preparation of a stable derivative of 1,2,5,6-heptatetraene.
Scheme 57: A bisallene with a carbonyl group as a spacer element.
Scheme 58: The first preparation of 1,2,6,7-octatetraene (242).
Scheme 59: Preparation of 1,2,6,7-octatetraenes by (C4 + C4)-coupling of enynes.
Scheme 60: Preparation of 1,2,6,7-octatetraenes by (C4 + C4)-coupling of homoallenyl bromides.
Scheme 61: Preparation of 1,2,6,7-octatetraenes by alkylation of propargylic substrates.
Scheme 62: Preparation of two highly functionalized 1,2,6,7-octatetraenes.
Scheme 63: Preparation of several higher α,ω-bisallenes.
Scheme 64: Preparation of different alkyl derivatives of α,ω-bisallenes.
Scheme 65: The preparation of functionalized 1,2,7,8-nonatetraene derivatives.
Scheme 66: Preparation of functionalized α,ω-bisallenes.
Scheme 67: The preparation of an α,ω-bisallene by direct homologation of an α,ω-bisalkyne.
Scheme 68: The gas-phase pyrolysis of 4,4-dimethyl-1,2,5,6-heptatetraene (237).
Scheme 69: Gas-phase pyrolysis of 1,2,6,7-octatetraene (242).
Scheme 70: The cyclopropanation of 1,2,6,7-octatetraene (242).
Scheme 71: Intramolecular cyclization of 1,2,6,7-octatetraene derivatives.
Scheme 72: The gas-phase pyrolysis of 1,2,7,8-nonatetraene (265) and 1,2,8,9-decatetraene (266).
Scheme 73: Rh-catalyzed cyclization of a functionalized 1,2,7,8-nonatetraene.
Scheme 74: A triple cyclization involving two different allenic substrates.
Scheme 75: Bicyclization of keto derivatives of 1,2,7,8-nonatetraene.
Scheme 76: The preparation of complex organic compounds from functionalized bisallenes.
Scheme 77: Cycloisomerization of an α,ω-bisallene containing a C9 tether.
Scheme 78: Organoborane polymers from α,ω-bisallenes.
Scheme 79: Preparation of trans- (337) and cis-1,2,4,6,7-octapentaene (341).
Scheme 80: The preparation of 4-methylene-1,2,5,6-heptatetraene (349).
Scheme 81: The preparation of acetylenic bisallenes.
Scheme 82: The preparation of derivatives of hydrocarbon 351.
Scheme 83: The construction of macrocyclic alleno-acetylenes.
Scheme 84: Preparation and reactions of 4,5-bismethylene-1,2,6,7-octatetraene (365).
Scheme 85: Preparation of 1,2-bis(propadienyl)benzene (370).
Scheme 86: The preparation of 1,4-bis(propadienyl)benzene (376).
Scheme 87: The preparation of aromatic and heteroaromatic bisallenes by metal-mediated coupling reactions.
Scheme 88: Double cyclization of an aromatic bisallene.
Scheme 89: Preparation of an allenic [15]paracyclophane by a ring-closing metathesis reaction of an aromatic α...
Scheme 90: Preparation of a macrocyclic ring system containing 1,4-bis(propadienyl)benzene units.
Scheme 91: Preparation of copolymers from 1,4-bis(propadienyl)benzene (376).
Scheme 92: A boration/copolymerization sequence of an aromatic bisallene and an aromatic bisacetylene.
Scheme 93: Formation of a layered aromatic bisallene.
Figure 4: The first members of the semicyclic bisallene series.
Scheme 94: Preparation of the first bis(vinylidene)cyclobutane derivative.
Scheme 95: Dimerization of strain-activated cumulenes to bis(vinylidene)cyclobutanes.
Scheme 96: Photodimerization of two fully substituted butatrienes in the solid state.
Scheme 97: Preparation of the two parent bis(vinylidene)cyclobutanes.
Scheme 98: The preparation of 1,3-bis(vinylidene)cyclopentane and its thermal isomerization.
Scheme 99: The preparation of the isomeric bis(vinylidene)cyclohexanes.
Scheme 100: Bi- and tricyclic conjugated bisallenes.
Scheme 101: A selection of polycyclic bisallenes.
Scheme 102: The first endocyclic bisallenes.
Figure 5: The stereochemistry of 1,2,6,7-cyclodecatetraene.
Scheme 103: The preparation of several endocyclic bisallenes.
Scheme 104: Synthesis of diastereomeric derivatives of 1,2,6,7-cyclodecatetraene.
Scheme 105: Preparation of a derivative of 1,2,8,9-cyclotetradecatetraene.
Scheme 106: The preparation of keto derivatives of cyclic bisallenes.
Scheme 107: The preparation of cyclic biscumulenic ring systems.
Scheme 108: Cyclic bisallenes in natural- and non-natural-product chemistry.
Scheme 109: The preparation of iron carbonyl complexes from cyclic bisallenes.
Figure 6: A selection of unknown exocyclic bisallenes that should have interesting chemical properties.
Scheme 110: The thermal isomerization of 1,2-diethynylcyclopropanes and -cyclobutanes.
Scheme 111: Intermediate generation of a cyclooctapentaene.
Scheme 112: Attempted preparation of a cyclodecahexaene.
Scheme 113: The thermal isomerization of 1,5,9-cyclododecatriyne (511) into [6]radialene (514).
Scheme 114: An isomerization involving a diketone derived from a conjugated bisallene.
Scheme 115: Typical reaction modes of heteroorganic bisallenes.
Scheme 116: Generation and thermal behavior of acyclic hetero-organic bisallenes.
Scheme 117: Generation of bis(propadienyl)thioether.
Scheme 118: The preparation of a bisallenic sulfone and its thermal isomerization.
Scheme 119: Bromination of the bisallenic sulfone 535.
Scheme 120: Metalation/hydrolysis of the bisallenic sulfone 535.
Scheme 121: Aromatic compounds from hetero bisallenes.
Scheme 122: Isomerization/cyclization of bispropargylic ethers.
Scheme 123: The preparation of novel aromatic systems by base-catalyzed isomerization of bispropargyl ethers.
Scheme 124: The isomerization of bisacetylenic thioethers to bicyclic thiophenes.
Scheme 125: Aromatization of macrocyclic bispropargylic sulfides.
Scheme 126: Preparation of ansa-compounds from macrocyclic bispropargyl thioethers.
Scheme 127: Alternate route for cyclization of a heterorganic bisallene.
Scheme 128: Multiple isomerization/cyclization of “double” bispropargylic thioethers.
Scheme 129: Preparation of a bisallenyl disulfide and its subsequent bicyclization.
Scheme 130: Thermal cyclization of a bisallenyl thiosulfonate.
Scheme 131: Some reactions of heteroorganic bisallenes with two sulfur atoms.
Scheme 132: Further methods for the preparation of heteroorganic bisallenes.
Scheme 133: Cyclization reactions of heteroorganic bisallenes.
Scheme 134: Thermal cycloadditions of bisallenic tertiary amines.
Scheme 135: Cyclization of a bisallenic tertiary amine in the presence of a transition-metal catalyst.
Scheme 136: A Pauson–Khand reaction of a bisallenic ether.
Scheme 137: Formation of a 2:1adduct from two allenic substrates.
Scheme 138: A ring-forming silastannylation of a bisallenic tertiary amine.
Scheme 139: A three-component cyclization involving a heterorganic bisallene.
Scheme 140: Atom-economic construction of a complex organic framework from a heterorganic α,ω-bisallene.
Beilstein J. Org. Chem. 2012, 8, 1505–1514, doi:10.3762/bjoc.8.170
Graphical Abstract
Scheme 1: Synthesis of PDOF-BT and PDOF-BTc copolymers.
Figure 1: 1H NMR spectrum (CDCl3) of the BTc inclusion complex.
Figure 2: FTIR spectra (KBr pellet) of PDOF-BT (A) and PDOF-BTc (B) copolymers.
Figure 3: 1H NMR spectrum of PDOF-BT copolymer (CDCl3).
Figure 4: 1H NMR spectrum of PDOF-BTc copolymer (CDCl3).
Figure 5: DSC curves of BTc and PDOF-BTc from second-heating DSC measurements.
Figure 6: Thermogravimetric curves (TG) for BTc, PDOF-BT, and PDOF-BTc compounds.
Figure 7: High-resolution tapping-mode AFM images and cross-section plots (along the solid line in the images...
Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4
Graphical Abstract
Figure 1: Schematic representation of organic D-π-A system featuring ICT.
Figure 2: Two principal orientations of the imidazole-derived charge-transfer chromophores.
Scheme 1: Common synthetic approach to triarylimidazole-, diimidazole-, and benzimidazole-derived CT chromoph...
Scheme 2: Syntheses of important 4,5-dicyanoimidazole derivatives 1–3 [27-30].
Figure 3: Donor–acceptor triaryl push–pull azoles 4a–h [31,32].
Figure 4: Y-shaped CT chromophores with an extended π-conjugated pathway and various donor and acceptor subst...
Figure 5: Molecular structures of chromophores 9–14 [13,15,37-41].
Figure 6: General structure of 4,5-bis(4-aminophenyl)imidazole-derived chromophores 15a–g with various π-link...
Figure 7: Various orientations of the substituents on the parent lophine π-conjugated backbone (16–19) and th...
Figure 8: Structure and electronic absorption spectra of chromophores 21–26 [12].
Figure 9: Typical D-π-A diimidazole CT chromophore [16-18,50-53].
Figure 10: Typical D-π-D diimidazoles 28–31 [19,54-56] and photochromic diimidazoles 32,33 [57,58].
Scheme 3: Oxidation of 1H-diimidazoles to 2H-diimidazoles (quinoids).
Figure 11: Typical benzimidazoles-derived D-π-A push–pull systems 35–43 [25,62-66].
Figure 12: Structure of benzimidazoles (44–47), imidazophenanthrolines (48–57), imidazophenanthrenes (58–60), ...
Scheme 4: Acidoswitchable NLO-phores 64,65 and ESIPT mechanism [72-74].
Figure 13: General structures of bis(benzimidazole) chromophores 67–71 and pyridinium betaines 72 [75-79].
Figure 14: Overview of 4,5-dicyanoimidazole derivatives investigated by Rasmussen et al. [29,81-94].
Figure 15: 4,5-Dicyanoimidazole-derived chromophores 84–87 [103-106].
Figure 16: Push–pull chromophores 88–93 with systematically extended π-linker [30].
Figure 17: pH-triggered NLO switches 88c–93c [109].
Figure 18: Dibromoolefin 94 and branched chromophores 95–100 [112,113].
Figure 19: Imidazole as a donor–acceptor unit in CT-chromophores 101–111 [20].
Figure 20: Diimidazoles 112–115 used as small electron acceptors in organic solar cells [115,116].
Figure 21: Amino- and hydroxy-functionalized chromophores incorporated into a polymer backbone Rpol [18,50-53,122-124].
Figure 22: Structure of polyphosphazene polymers bearing NLO-phores [125-127] and some other recent examples of nonline...
Figure 23: Epoxy- and silica-based polymers functionalized with 4,5-dicyanoimidazole unit [105,130].
Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92
Graphical Abstract
Figure 1: Structure of 3,6-diphenyl-substituted 2,5-diketopyrrolo[3,4-c]pyrrole (DPP).
Scheme 1: Synthesis of DPP monomers.
Figure 2: Plot of current density and light intensity versus voltage of polymer light-emitting diode containi...
Scheme 2: Pd-catalyzed coupling reactions for preparation of DPP-containing polymers.
Figure 3: Optical properties of some diphenylDPP-based conjugated polymers.
Figure 4: Optical properties of copolymers P-21 and P-22 based on two isomeric diphenylDPP monomer units (fro...
Figure 5: Absorption spectroelectrochemical plots of P-25 and P-26 as thin films on ITO glass. Scan rate: 100...
Scheme 3: Thiophenyl-DPP-based polymers.
Beilstein J. Org. Chem. 2010, 6, No. 79, doi:10.3762/bjoc.6.79
Graphical Abstract
Scheme 1: Synthesis of carbonitrile 1.
Scheme 2: Coupling of the β-DMCD-caged carbonitrile derivative 1-DMCD with PVAm to yield the fluorophore-func...
Figure 1: Solid state 13C-{1H}-CP-MAS NMR spectra of pure PVAm (a), functionalized PVAm 1-P (b) and the model...
Scheme 3: Synthesis of 1-Si by nucleophilic aromatic substitution of 1 adsorbed onto silica particles.
Figure 2: Wide-scan X-ray photoelectron spectra (left), C 1s and N 1s high-resolution spectra (right) of bare...
Figure 3: Pore-size distribution of bare silica, PVAm/silica and 1-Si.
Figure 4: UV–vis absorption and emission diffuse reflectance spectra of sample 1-Si.
Figure 5: Normalized absorption and emission spectra of 1-M (a) and 1-P (b).
Figure 6: Normalized emission spectra of 1-P in water at four different pH values and a sketch of the assumed...
Beilstein J. Org. Chem. 2010, 6, No. 12, doi:10.3762/bjoc.6.12
Graphical Abstract
Figure 1: The structure of the indolocarbazole-based chemosensor 1.
Scheme 1: Synthesis of receptor 1.
Figure 2: The AM1 optimized structure of receptor 1 (heat of formation = −8.29 kcal/mol).
Figure 3: Color changes of receptor 1 (A) (c = 1.1 × 10−4 M) in CH3CN/H2O (4:1 v/v) on addition of tetrabutyl...
Figure 4: UV spectral change of receptor 1 (c = 1.1 × 10−4 M) upon gradual addition of [Bu4N]+F− (left side) ...
Scheme 2: Schematic representation (the circles represent the indolocarbazole moiety) of the two-step process...
Figure 5: The Job plot of 1 with fluoride ion from UV method in CH3CN/H2O (4:1 v/v).
Figure 6: Fluorescence change of receptor 1 (c = 4.475 × 10−5 M) upon gradual addition of [Bu4N]+F− (left sid...
Figure 7: Binding constant calculation curves for receptor 1 vs F−, Cl−, Br−, I−, AcO−, HSO4−, and H2PO4− (le...
Figure 8: 1H NMR spectra of receptor 1 (bottom), 1 with [Bu4N]+F− 1:2 [receptor 1:(Bu4N)+F−] (middle) and exc...
Beilstein J. Org. Chem. 2009, 5, No. 11, doi:10.3762/bjoc.5.11
Graphical Abstract
Figure 1: Basic and newly proposed π-conjugated linkers designed for the Suzuki–Miyaura and Sonogashira cross...
Scheme 1: Convenient synthetic methods leading to π-linkers 3–6.
Scheme 2: Sonogashira cross-coupling leading to π-linkers 7c–9c.
Beilstein J. Org. Chem. 2009, 5, No. 6, doi:10.3762/bjoc.5.6
Graphical Abstract
Figure 1: Donors and acceptor compounds.
Scheme 1: Synthesis of π-extended dithiafulvalenes 7a and 7b. i) n-BuLi/THF, −78 °C, 15 min, then rt, overnig...
Scheme 2: Synthesis of π-extended dithiafulvalenes 8 and 9. i) 6, n-BuLi, THF, −78 °C, 15 min; then, 5c, −78 ...
Scheme 3: Synthesis of π-extended dithiafulvalenes 10. i) 6, n-BuLi, THF, −78 °C, 15 min; then 5d, −20 to 0 °...
Scheme 4: Synthesis of π-extended dithiafulvalenes 11 and dithiafulvalene 12. i) 6, n-BuLi, THF, −78 °C, 15 m...
Figure 2: Cyclic voltammetry (CV) of compounds 8, 10 and 11 in CH2Cl2 at scan rate 100 mV.