406491-06-3

Basic information

• Product Name: Benzenamine, 4-ethynyl-N,N-dihexyl-
• CAS NO: 406491-06-3
• Molecular Formula: C20H31N
• Molecular Weight: 285.473
• Mol File: 406491-06-3.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-ethynyl-N,N-dihexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-ethynyl-N,N-dihexyl-(406491-06-3)
• EPA Substance Registry System: Benzenamine, 4-ethynyl-N,N-dihexyl-(406491-06-3)

Safety Data

• Hazardous Substances Data: 406491-06-3(Hazardous Substances Data)

Upstream product

• 90134-09-1 N,N-dihexyl-4-iodobenzenamine 
• 1066-54-2 trimethylsilylacetylene 
• 111-25-1 1-bromo-hexane 
• 540-37-4 p-aminoiodobenzene 
• 638-45-9 1-Iodohexane 
• 689250-82-6 N,N-dihexyl-4-[2-(trimethylsilyl)ethynyl]benzenamine 
• 406491-04-1 4-[4-(dihexylamino)phenyl]-2-methyl-3-butyn-2-ol 

Downstream Products

• 406491-13-2 4-[[4-(dihexylamino)phenyl]ethynyl]benzaldehyde 
• 885515-80-0 4,4'-[1,4-phenylenebis(ethyne-2,1-diyl)]bis(N,N-dihexylaniline) 
• 1032401-49-2 2,6-bis{[4-(dihexylamino)phenyl]ethynyl}anthracene-9,10-dione 
• 745835-91-0 N,N-dihexyl-4-(3-{[4-(dihexylamino)phenyl]ethynyl}-6-(triisopropylsilyl)-4-[(triisopropylsilyl)ethynyl]-hex-3-ene-1,5-diyn-1-yl)benzenamine 
• 406491-11-0 1-(4-(N,N-dihexylamino)phenylethynyl)-4-iodobenzene 
• 958872-49-6 N,N'-di-(2',6'-diisopropylphenyl)-2,6-bis{2[4-(dihexylamino)phenyl]ethynyl}naphthalene-1,8,4,5-tetracarboxylic acid bisimide 
• 954105-32-9 N,N-dihexyl-4-[(triisopropylsilyl)buta-1,3-diyn-1-yl]aniline 

Relevant articles and documents

Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes

Seven three-ring phenylene-ethynylene (PE) structural analogs, differing only in the lengths of alkyl chains on terminal aniline substituents, show 50-62 nm bathochromic shifts in emission maxima in response to mechanical force (mechanofluorochromism, MC)

An improved singlet oxygen sensitizer with two-photon absorption and emission in the biological transparency window as a result of ground state symmetry-breaking

A chromophore featuring a diyne bridge that connects two dibromobenzene moieties shows a much improved two-photon singlet oxygen generation ability in the biological transparency window compared to a related and relevant literature benchmark, as a result

Influence of bromine substitution pattern on the singlet oxygen generation efficiency of two-photon absorbing chromophores

A molecular engineering strategy based on rational variations of the bromine substitution pattern in two-photon absorbing singlet oxygen sensitizers allows studying the relations that exist between the positioning of an inter-system crossing promoter on the charge-transfer chromophore and its ability to generate singlet oxygen. The Royal Society of Chemistry 2012.

From graftable biphotonic chromophores to water-soluble organic nanodots for biophotonics: The importance of environmental effects

The photophysical and two-photon absorption (TPA) properties of biphotonic chromophores with one or two phenol pendant units were studied and compared with that of a model biphotonic quadrupolar chromophore. A water-soluble dendritic structure was then sy

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.

On the route to mimic natural movements: Synthesis and photophysical properties of a molecular arachnoid

The synthesis, photoswitchability and NIR emitting properties of a novel π-extended pyrene derivative, peripherally decorated with four azobenzenyl-ethynyl legs, are reported.

New push-pull chromophores featuring TCAQ (11,11,12,12-Tetracyano-9,10- anthraquinodimethane) and other dicyanovinyl acceptors

Stable, highly colored push-pull chromophores with NMe2 donor and C=C(CN)2 acceptor moieties, featuring intense intramolecular charge-transfer (CT) bands in the UV/Vis spectra, are reported. In an attempt to prepare the quinoid pushpull systems 2, chromophores 10 and 11, with a central cyclohexene spacer, were obtained and characterized by X-ray analysis. A series of donor-substituted TCAQ (11,11,12,12-tetracyano-9,10-anthraquinodimethane) derivatives were synthesized, using the Knoevenagel condensation between appropriately functionalized anthraquinones and malononitrile, mediated by the Lehnert reagent (TiCl4/pyridine), as the key step. HCl addition to triple bonds was observed when this transformation was applied to alkynylated anthraquinones. Electrochemical studies by cyclic voltammetry (CV) and rotating-disk voltammetry (RDV) showed that introduction of donor substituents into the TCAQ core of 25, 26, and 31 shifts the first reduction potential to more negative values, while chromophores bearing guanidine moieties (27, 28) displayed a specific and complex redox behavior. Both electrochemical and UV/Vis data provide good evidence that D-A conjugation is more efficient through olefinic (in 10) than through acetylenic (in 37) spacers. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis, fluorescence, and two-photon absorption of a series of elongated rodlike and banana-shaped quadrupolar fluorophores: A comprehensive study of structure-property relationships

An extensive series of push-push and pull-pull derivatives was prepared from the symmetrical functionalization of an ambivalent core with conjugated rods made from arylene-vinylene or arylene-ethynylene building blocks, bearing different acceptor or donor

Hexasubstituted Donor-Acceptor Benzenes as Nonlinear Optically Active Molecules with Multiple Charge-Transfer Transitions

The synthesis of three novel nonlinear optical (NLO) chromophores with threefold symmetry, namely 1,3,5-tris(4-N,N-diethylaminophenyl)-2,4,6-tris(4-nitrophenyl)benzene (3), 1,3,5-tris(L-N,N-dihexylaminophenylbutadiynyl)-2,4,6-tris(4-nitrophenyl)benzene (1

Donor-substituted perethynylated dehydroannulenes and radiaannulenes: Acetylenic carbon sheets featuring intense intramolecular charge transfer

In this article, we report the preparation of unprecedented φ-conjugated macrocycles (Fig. 1) by acetylenic scaffolding using modular tetraethynylethene (TEE, 3,4-diethynylhex-3-ene-1,5-diyne) building blocks. A novel photochemical access to (Z)-bisdeprot