179925-08-7

Upstream product

• 116223-59-7 1-(dodecyloxy)-4-iodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 540-38-5 p-Iodophenol 
• 123883-51-2 1-bromo-4-dodecyloxybenzene 
• 106-41-2 4-bromo-phenol 
• 143-15-7 1-dodecylbromide 

Downstream Products

• 944245-03-8 C₆₈H₁₀₀N₄O₂S 
• 126835-82-3 4,4'-didodecyloxy-1,1'-diphenyl acetylene 
• 121051-42-1 1-(dodecyloxy)-4-ethynylbenzene 

Relevant academic research and scientific papers

Solid-Solid Phase Transitions in [ trans-Pt(PMe3)2(C=CC6H4R)2]-Containing Materials (R = O(CH2)nH; N = 6, 9, 12, and 15)

The title complexes were prepared in Hagihara conditions and were investigated by single crystal X-ray crystallography (n = 6, [Pt]C6; n = 12, [Pt]C12), X-ray powder diffraction (powder XRD), differential scanning calorimetry (DSC),

Pi-Extended Ethynyl 21,23-Dithiaporphyrins: A Synthesis and Comparative Study of Electrochemical, Optical, and Self-Assembling Properties

21,23-Dithiaporphyrins were synthesized containing pi-extending ethynyl substituents at the meso positions. These porphyrins displayed highly bathochromic and broadened absorbance profiles spanning 400-900 nm with molar absorptivities ranging from 2500 to 300,000 M-1 cm-1. Electrochemically, these ethynyl dithiaporphyrins undergo a single oxidation at 0.44 or 0.57 V and reduction at -1.17 or -1.08 V versus a ferrocene/ferrocenium internal standard depending on the type of functionalization appended to the ethynyl group. DFT calculations predict that the delocalization of the frontier molecular orbitals should expand onto the meso positions of the ethynyl 21,23-dithiaporphyrins; shrinking the HOMO-LUMO energy gap by destabilizing the HOMO energy. Indeed, the DFT results agree with our optical and electrochemical assessments. Finally, differential scanning calorimetry combined with cross-polarized optical microscopy and powder X-ray diffraction was used to assess the ability of these porphyrins for long-range order. For the ethynylphenyl alkoxy 21,23-dithiaporphyin, birefringent, soft-crystalline-like domains were observed by polarized microscopy, which are marginally sustained by a low-level of crystallinity detected in the XRD, suggesting that long-range ordering is possible. Overall, ethynyl 21,23-dithiaporphyrins are able to harvest much lower energy light and possess lower oxidation and reduction potentials compared to their pyrrolic analogues, which are desirable properties for applications in organic electronics.

Enhanced anhydrous proton conduction in binary mixtures of 1H-imidazole-1H-1,2,3-triazole based compounds

What is the impact of mixing two proton-conducting heterocycles on proton conductivity? Herein we answer this question through our investigations on two linear rod-like compounds 2-(4-(dodecyloxy)phenyl)-1H-imidazole (4) and 5-(4-(dodecyloxy)phenyl)-1H-1,

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.

Functionalizable polycyclic aromatics through oxidative cyclization of pendant thiophenes

We present a general strategy for obtaining large sulfur-containing polycyclic aromatics from thienyl precursors through iron(Ill) chloride mediated oxidative cyclizations. By placing thienyl moieties in close proximity to adjacent arenes, we have directed the oxidized intermediates into controlled cyclization pathways, effectively suppressing polymer formation. Utilizing these cyclized compounds and their thienyl precursors, we have studied cyclization/polymerization pathways of polymers such as poly(2). The unsubstituted positions α to the sulfur atoms within these aromatic cores allowed for efficient halogenation and further functionalization. As a demonstration, we prepared a series of arylene-ethynylene polymers with varying degrees of chromophore aromatization and used them to probe the effects of synthetically imposed rigidity on polymer photophysical behavior. The symmetries and effective conjugation pathways within the monomers play a key role in determining photophysical properties. We observed that rigid, aromatized chromophores generally led to increased excited-state lifetimes by decreasing radiative rates of fluorescence decay.

Solid dimorphism of tetra-arylcyclobutadienecobalt derivatives bearing long aliphatic lateral groups

A new series of disk-like cyclobutadienecobalt derivatives symmetrically substituted by lateral alkoxy groups with different chain lengths (-O(CH2)nCH3, n=5, 6, 8, and 12) were prepared and their thermal phase transition b

Template-mediated synthesis of polycyclic aromatic hydrocarbons: Cyclodehydrogenation and planarization of a hexaphenylbenzene derivative at a copper surface

The deposition of polycyclic aromatic hydrocarbons on substrate surfaces is a key step for using such disklike molecules in nanoelectronic devices. An alternative to the (frequently problematic) preparation by evaporation or deposition from solution is to

Enhanced Aggreagtion of Derivatized Tolan Surfactants through Donor-Acceptor Interactions at the Air-Water Interface and in Langmuir-Blodgett Films

Control of aggregation behavior of derivatized surfactants by moderately polar functional groups as well as the role of charge-transfer interactions governing photophysical phenomena was studied using surfactants incorporating the diphenylacetylene (tolan