153033-27-3

Usage

Uses

Used in Organic Chemistry:
Benzene, 1,4-diethynyl-2,5-bis(octyloxy)is used as a building block for the synthesis of various functional materials due to its unique structure and properties. It plays a crucial role in the development of advanced materials and technologies in the field of organic electronics and optoelectronics.
Used in Chemical and Materials Industries:
The long hydrophobic chains of Benzene, 1,4-diethynyl-2,5-bis(octyloxy)provide solubility in non-polar solvents, making it suitable for use in various applications within the chemical and materials industries. Its versatility in synthesis and compatibility with different solvents contribute to its wide range of uses in these sectors.
Used in Organic Electronics:
Benzene, 1,4-diethynyl-2,5-bis(octyloxy)is used as a component in the development of organic semiconductors, which are essential for creating flexible and efficient electronic devices. Its structural features contribute to the performance and properties of these semiconductors.
Used in Optoelectronics:
In the field of optoelectronics, Benzene, 1,4-diethynyl-2,5-bis(octyloxy)is utilized for the synthesis of materials with specific optical properties. Its incorporation into optoelectronic devices can enhance their performance and enable new functionalities.
Used in the Synthesis of Liquid Crystals:
Benzene, 1,4-diethynyl-2,5-bis(octyloxy)is also used in the synthesis of liquid crystals, which are vital for display technologies and other applications that require responsive and tunable optical properties.
Each of these applications leverages the unique structural attributes and chemical properties of Benzene, 1,4-diethynyl-2,5-bis(octyloxy)-, highlighting its importance in the advancement of modern materials science.

Upstream product

• 994-89-8 tributylethynyltin 
• 145483-68-7 1,4-diiodo-2,5-dioctyloxybenzene 
• 111-83-1 1-bromo-octane 
• 150-78-7 1,4-dimethoxybezene 
• 51560-21-5 1,4-diiodo-2,5-dimethoxybenzene 
• 123-31-9 hydroquinone 
• 173428-81-4 1,4-bis[(trimethylsilyl)-ethynyl]-2,5-bis-(octoxy)benzene 
• 156028-40-9 1,4-dibromo-2,5-dioctyloxyphenylene 
• 67399-94-4 1,4-bis(octyloxy)benzene 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 133069-19-9 1,4-Bis-{(E)-2-[dimethyl-((E)-styryl)-silanyl]-vinyl}-2,5-bis-octyloxy-benzene 
• 530087-29-7 trans-[Pt(P(n-Bu)3)2(CC(C₆H₂(O-n-C₈H₁₇)2-2,5)CC)] 
• 1186589-62-7 C₄₀H₅₀O₄ 
• 1233845-66-3 1,4-bis((6-methylpyridazin-3-yl)ethynyl)-2,5-dioctyloxybenzene 
• 1300743-85-4 1-decyl-4-(4-(1-decyl-1H-1,2,3-triazol-4-yl)-2,5-bis(octyloxy)phenyl)-1H-1,2,3-triazole 
• 944245-14-1 C₇₈H₁₀₀N₆O₂S₂ 
• 1240562-47-3 C₉₀H₁₀₈B₂N₄O₄ 
• 1400937-71-4 5,5′-((2,5-dioctyl-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-hydroxy-3-(piperidin-1-ylmethyl))benzaldehyde 
• 1430403-87-4 2,5-dioctyloxy-1,4-bis(1-propynyl)benzene 
• 1215068-99-7 [Ru(II)Cl(CO)(PMe3)3]2(μ-CH=CH-C6H2(O-n-C8H17)2-CH=CH) 
• 431898-27-0 1,4-bis(4-formyl-2,5-dioctyloxyphenylethynyl)-2,5-dioctyloxybenzene 

Relevant academic research and scientific papers

A joint experimental and computational study on the electronic communication in diethynylaryl-bridged (η5-C5H 5)Fe(η2-dppe) and (η5-C 5H5)-Fe(CO)2 units

A family of bimetallic complexes [Cp(CO)2Fe-C≡C-Ar- C≡C-Fe(CO)2Cp] {Cp = C5H5; 6a-g: Ar = C4H2S (a), 3-(C4H9)-C4HS (b), 3-(C16H33)-C4HS (c), C6H 4 (d), 2,5-bis-(OC4H9)-C6H 2 (e), 2,5-bis(OC8H17)-C6H 2 (f), (C6H4)2 (g)} was prepared by the three-step Pd-catalysed extended one-pot (EOP) synthetic protocol from Bu3Sn-C≡CH, X-Ar-X (X = I, Br) and Cp(CO)2FeI. Complexes 6a,d,g were then exposed to ultraviolet irradiation in the presence of an equivalent amount of 1,2-bis(diphenylphosphanyl)ethane (dppe) to form the corresponding bimetallic complexes [Cp(dppe)Fe-C≡C-Ar-C≡C-Fe(dppe) Cp] (7a,d,g). Compounds 6a-g and 7a,d,g were characterised by cyclic voltammetry (CV). The most significant electrochemical information comes from the oxidation of the dppe derivatives. The ΔE° separations between the subsequent reversible waves suggest that the efficiency of the metal-metal electronic coupling decreases in the order 7a > 7d > 7g. Complexes 7a and 7g were also chemically oxidised with [Fe(Cp*]2[BF4] {Cp* = C5(CH3)5} and [Fe(Cp)] 2[BF4] respectively, and the near infrared (NIR) spectra of the mixed-valence species 7a+ and 7g+ were recorded. A strong intervalence transition (IT) band was observed only for the radical cation 7a+. While this finding confirms the existence of an electronic interaction between the two termini when a 2,5-thiophene group is present in the spacer, the NIR spectrum of 7g+ reveals a reduced efficiency in conveying electrons when the C4H2S moiety is replaced by a 4,4′-biphenyl. In order to rationalise and quantify the extent of electronic communication, ruled by geometrical and electronic factors, density functional computational results on selected [Cp (PH3) 2Fe] and [Cp(CO)2Fe] binuclear model complexes are reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

How Large Can We Build a Cyclic Assembly? Impact of Ring Size on Chelate Cooperativity in Noncovalent Macrocyclizations

Self-assembled systems rely on intramolecular cooperative effects to control their growth and regulate their shape, thus yielding discrete, well-defined structures. However, as the size of the system increases, cooperative effects tend to dissipate. We analyze here this situation by studying a set of oligomers of different lengths capped with guanosine and cytidine nucleosides, which associate in cyclic tetramers by complementary Watson–Crick H-bonding interactions. As the monomer length increases, and thus the number of C(sp)–C(sp2) σ-bonds in the π-conjugated skeleton, the macrocycle stability decreases due to a notable reduction in effective molarity (EM), which has a clear entropic origin. We determined the relationship between EM or ΔS and the number of σ-bonds, which allowed us to predict the maximum monomer lengths at which cyclic species would still assemble quantitatively, or whether the cyclic species would not able to compete at all with linear oligomers over the whole concentration range.

White light emission from fluorene-EDOT and phenothiazine-hydroquinone based D-π-A conjugated systems in solution, gel and film forms

Two conjugated D-π-A organic molecules, one fluorene-ethylene dioxythiophene (FL-E) based and another phenothiazine-hydroquinone (PT-Hq) based, were synthesized and observed to form 1-dimensional microstructures in the solid state. These two molecules whe

Polymer-based fluorescence sensor incorporating thiazole moiety for direct and visual detection of Hg2+ and Ag+

A thiazole-based conjugated polymer was synthesized by the polymerization reaction of 4,7-dibromo-2-methylbenzo[d]thiazole with 1,4-diethynyl-2,5-bis(octyloxy)benzene via Pd-catalyzed Sonogashira coupling reaction. The conjugated polymer emits bright green fluorescence and exhibits 'turn-off' fluorescent quenching responses towards both Hg2+ and Ag+ over other cations, such as Li+, K+, Ca2+, Mg2+, Ba2+, Zn2+, Cd2+, Co2+, Ni2+, Pb2+, Cu2+, Al3+ and Fe3+. More importantly, the color change of this polymer solution could be clearly observed by the naked eyes upon the addition of Hg2+ (green to colorless) and Ag+ (green to yellow), indicating that this thiazole-based conjugated polymer material could be used as a colorimetric sensor for directly visual detection of Hg2+ and Ag+.

Boron ketoiminate-based conjugated polymers with tunable AIE behaviours and their applications for cell imaging

Three new boron ketoiminate-based conjugated polymers P1, P2, and P3 were designed and synthesized through the Sonogashira coupling reaction of 4,6-bis(4-bromophenyl)-2,2-difluoro-3-phenyl-2H-1,3,2-oxazaborinin-3-ium-2-uide (M1) with 1,4-diethynyl-2,5-bis

Supramolecular ruthenium-alkynyl multicomponent architectures: Engineering, photophysical properties, and responsiveness to nitroaromatics

A series of H-bonded supramolecular architectures were built from monofunctional M-Ci - C-R and bifunctional R-Ci - C-M-Ci - C-R trans-alkynylbis(1,2-bis(diphenylphosphino)ethane)ruthenium(II) complexes and π-conjugated modules containing 2,5-dialkoxy-p-p

Encapsulation-induced remarkable stability of a hydrogen-bonded heterocapsule

Remarkably enhanced stability of the self-assembled hydrogen-bonded heterocapsule 1×2 by the encapsulation of 1,4-bis(1-propynyl)benzene 3 a was found with Ka=1.14×109 M-1 in CDCl3 and Ka2=1.59×108 M-2 in CD3OD/CDCl3 (10 % v/v) at 298 K. The formation of 3 a(1×2) was enthalpically driven (ΔH°0 and ΔS°0) and there was a unique inflection point in the correlation between ΔH° versus ΔS° as a function of polar solvent content. The ab initio calculations revealed that favorable guest-capsule dispersion and electrostatic interactions between the acetylenic parts (triple bonds) of 3 a and the aromatic inner space of 1×2, as well as less structural deformation of 1×2 upon encapsulation of 3 a, play important roles in the remarkable stability of 3 a(1×2). Copyright

In situ generated 1:1 Zn(II)-containing polymer complex sensor for highly enantioselective recognition of N-Boc-protected alanine

A novel chiral (S)-BINAM-based fluorescence polymer sensor was designed and synthesized by the polymerization of 5,5′-((2,5-dioctyloxy-1,4-phenylene) bis(ethyne-2,1-diyl)bis(2-hydroxy-3-(piperidin-1-ylmethyl)benzaldehyde (M-1) with (S)-2,2′-binaphthyldiamine (S-BINAM, M-2) via Schiffs base formation. The resulting chiral polymer sensor shows very weak fluorescence but exhibits the obvious fluorescence enhancement response toward Zn2+. The in situ generated 1:1 Zn(II)-containing complex of chiral polymer can serve as a fluorescence sensor for highly enantioselective recognition of N-Boc-protected alanine, and the value of enantiomeric fluorescence difference ratio (ef) can reach as high as 6.90. This is the first report on the in situ generated chiral polymer complex used as a fluorescence sensor for highly enantioselective recognition of N-Boc-protected alanine.

Two-photon absorption properties of proquinoidal D-A-D and A-D-A quadrupolar chromophores

We report the synthesis, one- and two-photon absorption spectroscopy, fluorescence, and electrochemical properties of a series of quadrupolar molecules that feature proquinoidal p-aromatic acceptors. These quadrupolar molecules possess either donoracceptor donor (D-A-D) or acceptordonoracceptor (A-D-A) electronic motifs, and feature 4-N,N-dihexylaminophenyl, 4-dodecyloxyphenyl, 4-(N,N-dihexylamino)benzo[c][1,2,5]thiadiazolyl or 2,5-dioctyloxyphenyl electron donor moieties and benzo[c][1,2,5]thiadiazole (BTD) or 6,7-bis(30,70-dimethyloctyl)[1,2,5]thiadiazolo[3,4-g]quinoxaline (TDQ) electron acceptor units. These conjugated structures are highly emissive in nonpolar solvents and exhibit large spectral red-shifts of their respective lowest energy absorption bands relative to analogous reference compounds that incorporate phenylene components in place of BTD and TDQ moieties. BTD-based D-A-D and A-D-A chromophores exhibit increasing fluorescence emission redshifts, and a concomitant decrease of the fluorescence quantum yield (Ff) with increasing solvent polarity; these data indicate that electronic excitation augments benzothiadiazole electron density via an internal charge transfer mechanism. The BTD- and TDQcontaining structures exhibit blue-shifted two-photon absorption (TPA) spectra relative to their corresponding one-photon absorption (OPA) spectra, and display high TPA cross sections (>100 GM) within these spectral windows. D-A-D and A-D-A structures that feature more extensive conjugation within this series of compounds exhibit larger TPA cross sections consistent with computational simulation. Factors governing TPA properties of these quadrupolar chromophores are discussed within the context of a three-state model.

Synthesis of π-conjugated polymers via regioregular organometallic polymers 2. Transformation of titanacyclopentadienecontaining polymer into poly(ρ-phenylene) derivative

The transformation of a regioregular organometallic polymer possessing titanacyclopentadiene-2,5-diyl units into a poly(ρ-phenylene) derivative by means of a novel polymer reaction method is described. The organotitianium polymer was prepared by the polymerization of 1,4-diethynyl-2,5- dioctyloxybenzene and a low-valent titanium complex, generated in situ from titanium(IV) isopropoxide and isopropylmagnesium chloride, and was subjected to the reaction with 3-bromo-1-propyne followed by the protonation. Consequently, a polymer consisting of the substituted phenylene-1,4-diyl units could be produced in a high yield,which is soluble in organic solvents such as chloroform. The number-average molecularweight and themolecular weight distribution of the polymer were estimated as 4800 and 1.8, respectively (GPC, polystyrene). The UV-vis absorption spectrum of the polymer exhibited the absorption maximum (λmax) at 329 nm, which was bathochromically shifted by 53 nm compared with that of a model compound, 1,4-bis(2-methoxyphenyl)-2- methylbenzene (λmax = 276 nm). Copyright