30405-78-8

Usage

Uses

Used in Electronics Industry:
4,4'-(buta-1,3-diyne-1,4-diyl)dianiline is used as a component in the production of conducting polymers for its ability to facilitate charge transport, making it valuable in electronic devices and components.
Used in Aerospace Industry:
In aerospace, 4,4'-(buta-1,3-diyne-1,4-diyl)dianiline is utilized as a material in the development of high-performance fibers, which are essential for the construction of lightweight and strong aerospace components.
Used in Automotive Industry:
4,4'-(buta-1,3-diyne-1,4-diyl)dianiline is employed in the automotive sector for its role in flame retardant materials, enhancing the safety features of vehicles by reducing the risk of fire.
Used in Organic Synthesis:
BDAD is used as a versatile building block in organic synthesis for the creation of a variety of chemical compounds, highlighting its importance in chemical research and development.
Safety Note:
It is important to acknowledge that 4,4'-(buta-1,3-diyne-1,4-diyl)dianiline is toxic to aquatic organisms. Therefore, it must be handled and disposed of with appropriate care and precautions to mitigate environmental impact.

Upstream product

• 30405-77-7 1,4-bis(p-nitrophenyl)butadyine 
• 14235-81-5 4-Ethynylaniline 
• 566163-88-0 methyl ester of N-(tert-butoxycarbonyl)-β,β-dibromodehydroalanine 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 24393-61-1 ethyl (E)-3-(4-nitrophenyl)-2-propenoate 
• 861718-54-9 (Ph₃P)AuCCCCAu(PPh₃) 
• 540-37-4 p-aminoiodobenzene 
• 51560-25-9 1,4-diiodo-2,3-dimethoxybenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 536-74-3 phenylacetylene 
• 42472-69-5 4-ethynylacetophenone 
• 768-60-5 4-methoxyphenylacetylen 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 317842-48-1 tert-butyl (4-ethynylphenyl)carbamate 

Downstream Products

• 552299-18-0 1,4-bis-(4'-azidophenyl)butadiyne 
• 1234622-41-3 1-{4-[4-(4-aminophenyl)buta-1,3-diyn-1-yl]phenyl}-1'-hexyl-4,4'-bipyridinium bromide chloride 
• 1234622-42-4 1-{4-[4-(4-aminophenyl)buta-1,3-diyn-1-yl]phenyl}-4,4'-bipyridinium chloride 
• 847900-39-4 1,4-bis(p-propionamidophenyl)butadiyne 

Relevant academic research and scientific papers

Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes

Several phenylacetylenes were coupled under Sonogashira cross-coupling conditions with the methyl esters of N-(tert-butoxycarbonyl)-(E)-β-bromo- or -β,β-dibromodehydroalanine, to give β-substituted or β,β-disubstituted dehydroalanines, respectively. The β-substituted dehydroalanines were obtained in good to high yields (60-90%) under the usual Sonogashira conditions (1 equiv. of the phenylacetylene, 1 mol % of [Pd(PPh3)4], 2 mol % of CuI, 18 equiv. of NEt 3 in acetonitrile, 24 h at room temp.), with retention of stereochemistry. The β,β-disubstituted dehydroalanines were, in turn, obtained in moderate to good yields (44-63%) under modified Sonogashira conditions (4 equiv. of the phenylacetylene, 10 mol % of [PdCl 2(PPh3)2], 20 mol % of CuI, 1.4 equiv. of Cs2CO3 in acetonitrile, 2 h at reflux). In the latter reactions, some phenylacetylene dimer and the (E) isomer of the monosubstituted coupled products were also isolated to some extent. The Sonogashira products obtained from the 4-bromophenylacetylene were allowed to react with functionalized benzo[b]thiophenes under C-C or C-N palladium-catalyzed cross-coupling conditions. Preliminary fluorescence studies were performed for mono- and disubstituted (4-aminophenyl)acetylenic dehydroamino acids and for the benzo[b]-thiophene derivatives. The results showed that some of the dehydroalanines prepared can be used as fluorescent probes. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Rational Design of Diphenyldiacetylene-Based Fluorescent Materials Enabling a 365-nm Light-Initiated Topochemical Polymerization

Photopolymerization of diacetylenes usually requires stringent reaction conditions like high energy irradiation of 254-nm light or even γ-rays, which are generally harmful to the human body and thus mild conditions with lower energy irradiation are requir

Integrative self-sorting synthesis of a Fe8Pt6L 24 cubic cage

96 bonds were formed when 62 building blocks (heterotopic ligands with FeII and PtII ions) self-assembled in a one-pot reaction into a heterometallic Fe8Pt6L24 cubic cage (see model, Fe purple, Pt orange, N blue). The dynamic nature of this method also allowed an efficient cage-to-cage conversion: a tetrahedral Fe4L 6 cage was converted into the Fe8Pt6L 24 cube, which was subsequently converted into a second tetrahedral Fe4L'6 cage. Copyright

Creating Dynamic Nanospaces in Solution by Cationic Cages as Multirole Catalytic Platform for Unconventional C(sp)?H Activation Beyond Enzyme Mimics

Herein we demonstrate that, based on the creation of dynamic nanospaces in solution by highly charged positive coordination cage of [Pd6(RuL3)8]28+, multirole and multi-way cage-confined catalysis is accomplisha

Diacetylene Functionalized Covalent Organic Framework (COF) for Photocatalytic Hydrogen Generation

Covalent organic frameworks (COFs) are crystalline, highly porous, two- or three-dimensional polymers with tunable topology and functionalities. Because of their higher chemical stabilities in comparison to their boron-linked counterparts, imine or β-ketoenamine linked COFs have been utilized for a broad range of applications, including gas storage, heterogeneous catalysis, energy storage devices, or proton-conductive membranes. Herein, we report the synthesis of highly porous and chemically stable acetylene (-C≡C-) and diacetylene (-C≡C-C≡C-) functionalized β-ketoenamine COFs, which have been applied as photocatalyst for hydrogen generation from water. It is shown that the diacetylene moieties have a profound effect as the diacetylene-based COF largely outperforms the acetylene-based COF in terms of photocatalytic activity. As a combined effect of high porosity, easily accessible diacetylene (-C≡C-C≡C-) functionalities and considerable chemical stability, an efficient and recyclable heterogeneous photocatalytic hydrogen generation is achieved.

Copper Catalysis for Selective Heterocoupling of Terminal Alkynes

A Cu-catalyzed selective aerobic heterocoupling of terminal alkynes is disclosed, which enables the synthesis of a broad range of unsymmetrical 1,3-diynes in good to excellent yields. The results disprove the long-held belief that homocouplings are exclusively favored in the Glaser-Hay reaction.

Electronic properties of hyperbranched compounds derived by pyrrole

The electronic structure of hyperbranched polymers obtained from para-diaminodiphenyldiacetylenes as AB2 type monomers by one-step polymerization is studied using DFT calculations. Five generations are modelled with optimization at each step. As the molecule grows it shows a helical shape conserving the C2 symmetry with wing like fragments covering the backbone. There is accidental degeneracy of the HOMO with the HOMO-1 and of the HOMO-2 with the HOMO-3. The LUMO is always located at the backbone and the HOMO set at the dianyline-pyrrole fragment. The HOMO-LUMO gap decreases as the molecule grows. Conductivity measurements as well as microscopy studies of para-hyperbranched polymer were carried out. Conductivity measurements as a function of temperature show semiconductor behavior. Optical microscopy reveals a macroscopic crystalline structure of this hyperbranched polymer.

Single-molecule conductance of functionalized oligoynes: Length dependence and junction evolution

We report a combined experimental and theoretical investigation of the length dependence and anchor group dependence of the electrical conductance of a series of oligoyne molecular wires in single-molecule junctions with gold contacts. Experimentally, we focus on the synthesis and properties of diaryloligoynes with n = 1, 2, and 4 triple bonds and the anchor dihydrobenzo[b]thiophene (BT). For comparison, we also explored the aurophilic anchor group cyano (CN), amino (NH2), thiol (SH), and 4-pyridyl (PY). Scanning tunneling microscopy break junction (STM-BJ) and mechanically controllable break junction (MCBJ) techniques are employed to investigate single-molecule conductance characteristics. The BT moiety is superior as compared to traditional anchoring groups investigated so far. BT-terminated oligoynes display a 100% probability of junction formation and possess conductance values which are the highest of the oligoynes studied and, moreover, are higher than other conjugated molecular wires of similar length. Density functional theory (DFT)-based calculations are reported for oligoynes with n = 1-4 triple bonds. Complete conductance traces and conductance distributions are computed for each family of molecules. The sliding of the anchor groups leads to oscillations in both the electrical conductance and the binding energies of the studied molecular wires. In agreement with experimental results, BT-terminated oligoynes are predicted to have a high electrical conductance. The experimental attenuation constants βH range between 1.7 nm-1 (CN) and 3.2 nm-1 (SH) and show the following trend: β H(CN) H(NH2) H(BT) H(PY) ≈ βH(SH). DFT-based calculations yield lower values, which range between 0.4 nm -1 (CN) and 2.2 nm-1 (PY).

Ligand-free copper-catalyzed synthesis of symmetrical diynes from 1,1-dibromo-1-alkenes

Symmetrical diynes were synthesized by ligand-free copper-catalyzed homocoupling reaction of 1,1-dibromo-1-alkenes using a DBU/DMSO system at room temperature in good to excellent yields.

Cross-coupling reactions of gold(I) alkynyl and polyyndiyl complexes

Gold(I) alkynyl complexes are shown to efficiently couple with aryl iodides under mild conditions in the presence of both Pd(II) and Cu(I) co-catalysts. The reaction is not gold catalysed, but rather the Au(I) centre serves to transfer the alkynyl moiety to Cu(I), which then enters the conventional Sonogashira cycles. Using this method, a small range of 1,4-disubstituted diynes, including examples of differentially substituted compounds ArCCCCAr′, have been prepared directly from [(Ph3P) AuCCCCAu(PPh3)] and aryl iodides ArI.