9,9-Bis[4-(2-acryloyloxyethyloxy)phenyl]fluorene

• CAS: 161182-73-6
• Catalog Number: ACM161182736
• Category: Main Products
• Molecular Weight: 546.61
• Molecular Formula: C₃₅H₃₀O₆
• Synonyms: 9,9-BIS[4-(2-ACRYLOYLOXYETHYLOXY)PHENYL]FLUORENE;2-Propenoic acid 9H-fluoren-9-ylidene-bis(4,1-phenyleneoxy-2,1-ethanediyl) ester;9,9-BIS[4-(2-ACRYLOYLOXYETHOXY)PHENYL]FLUORENE;9,9-Bis[4-2-Acryloloxyethoxy)phenyl] fluorene;9,9-Bis(4-(2-acryloxyethoxy)phenyl)fluorene;(((9H-Fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl) diacrylate
• IUPAC Name: 2-[4-[9-[4-(2-prop-2-enoyloxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethylprop-2-enoate
• Canonical SMILES: C=CC(=O)OCCOC1=CC=C(C=C1)C2(C3=CC=CC=C3C4=CC=CC=C42)C5=CC=C(C=C5)OCCOC(=O)C=C
• InChI Key: YCPMSWJCWKUXRH-UHFFFAOYSA-N
• Boiling Point: 671.3ºC at 760 mmHg
• Density: 1.208
• Exact Mass: 546.20400

Case Study

Poly(9,9'-Bis[4-(2-Acryloyloxyethyloxy)Phenyl]Fluorene) Polymer Microspheres for Super-Resolution Imaging

Zhu, Haie, et al. Macromolecules, 2017, 50(2), 660-665.

This research successfully created high-refractive-index, shape-controllable colloidal polymer microspheres specifically designed for solid immersion lenses using poly(9,9'-bis[4-(2-acryloyloxyethyloxy)phenyl]fluorene) (poly(BAEPF)). The produced SILs based on polymer microspheres serve multiple applications including super-resolution imaging together with optical storage, spectral signal enhancement and near-field lithography among other fields.
Synthesis of Polymer Microspheres
· The synthesis of Poly(BAEPF) colloidal microspheres was performed through suspension polymerization. During this procedure 0.07 g of PVA dissolved in 120 g deionized water was heated to reach 65 °C for 10 minutes to yield a 0.058 wt % PVA solution before cooling to room temperature.
· After cooling the PVA solution to room temperature, introduced a uniform oil mixture containing 0.35 g of BAEPF, 0.5 g of CHCl3, 0.005 g of LPO, and 0.006 g of photoinitiator-184 to the PVA solution. The homogenizer mixed the solution at 6000 rpm for 3 minutes and then CHCl3 was removed using rotary evaporation at 150 rpm and 40 °C for 40 minutes.
· The dispersion product was placed into a 250 mL four-neck round-bottom flask that contained a mechanical stirrer, thermocouple, reflux condenser, and nitrogen gas inlet. After degassing with nitrogen for 30 minutes the system reached 75 °C and stirred at 250 rpm for 7 hours to enable polymerization which produced polymer colloidal microspheres. The monomers' high viscosity restricted the conversion rate to around 60%.

9,9'-Bis[4-(2-acryloyloxyethoxy)phenyl]fluorene for optical super-resolution imaging studies

Zhu, Haie, et al. ACS nano 10.10 (2016): 9755-9761.

Optical microscopy is a widely used real-time research tool, but usually suffers from low resolution due to the Abbe diffraction limit. ZrO2/polymer hybrid colloidal microspheres with up to 47.5 wt% inorganic nanoparticles were designed and successfully synthesized by suspension polymerization of 9,9'-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (BAEPF). Due to the uniform dispersion, high density and high refractive index of inorganic nanoparticles and the deformability of the polymer, the obtained ZrO2/poly(BAEPF) hybrid colloidal microspheres have high refractive index, optical transparency and controllable curvature, so they can be directly used as hybrid solid immersion lenses (hSILs) for optical microscopy, achieving super-resolution imaging of 50nm or even 45nm under standard white light or blue light optical microscopy, far beyond the diffraction limit of visible light optical microscopy.
ZrO2/Poly9,9'-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (BAEPF) mixed colloidal microspheres were synthesized by suspension polymerization. Typically, polyvinyl alcohol (PVA) was added to deionized water, heated to 65°C for 15 min to obtain a 0.054wt% PVA aqueous solution, which was then cooled to room temperature. Then, a homogenized oil phase containing different amounts of MPS/ZrO2 dispersed in 0.8 g CHCl3, 0.18 g 9,9'-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, and 0.0068 g lauroyl peroxide was poured into the PVA aqueous solution. After emulsification at 6000 rpm for 3 min using a homogenizer, CHCl3 in the mixture was removed by evaporation at 150 rpm and 40°C for 40 min using a rotary evaporator. Subsequently, the dispersion was poured into a 250 mL four-necked round-bottom flask equipped with a mechanical stirrer, a thermocouple, a reflux condenser, and a nitrogen inlet. The system was degassed with nitrogen for 30 min and then heated to 75 °C for polymerization at 250 rpm for 6 h under a nitrogen atmosphere to obtain hybrid colloidal microspheres containing 15.7, 26.0, and 47.5 wt% ZrO2 nanoparticles, which were denoted as S1, S2, and S3, respectively.

9-Bis(4-(2-acryloyloxyethyloxy)phenyl)fluorene resin to study UV curing methods

Oakdale, James S., et al. Optics express 24.24 (2016): 27077-27086.

Two-photon polymerization (TPP) is a precise, reliable and increasingly popular technique for rapid prototyping of micro-components with submicron resolution. The materials of choice for this process are primarily acrylic resins that are crosslinked by free radical polymerization. Due to the nature of the printing process, the derived parts are only partially cured, and the corresponding mechanical properties (i.e., modulus and ultimate strength) are lower than when the material is maximally crosslinked. The researchers studied the overall crosslinking degree of TPP derived structures by using TPP resin made from 9-Bis(4-(2-acryloyloxyethyloxy)phenyl)fluorene.
The TPP resin, which consists of only two components, PETA prepared from 9-Bis(4-(2-acryloyloxyethyloxy)phenyl)fluorene and 0.1wt% of 4,4-bis(diphenylamino)stilbene photoinitiator (BPASPI), has a large cross-sectional area of TPA. A series of wood stakes were printed in 0.11 TW/cmin DiLL mode with a 25x0.8NA objective and subjected to multiple curing procedures before air drying, including post-print UV curing with and without DMPA, without additional curing steps, as shown in Figure 5. Subsequent Raman analysis showed an average DC value of 22% ± 2 for the printed samples.