Article
Macromolecules, Vol. 44, No. 2, 2011 209
Alliance 2695 separations module and a Viscotek TDA model
302 consisting of a RI detector at a wavelength of 660 nm, a
4-capillary viscometer, and a 7ꢀ light scattering detector (LS) in
3 mW power at a wavelength of 670 nm were used for these
samples. Two Polymer Laboratories Polypore columns (300 ꢀ
7.5 mm, 5 μm) were used, and the detectors were temperature
controlled in the same oven as the Viscotek TDA. Measure-
ments were done at 40 ꢀC with THF as the mobile phase at a flow
rate of 1.0 mL/min; dn/dc was allowed to float between 0.133
and 0.138 mL/g. Each sample was injected three times, and the
data were mathematically averaged before processing. The third
SEC characterization (SEC-3) was performed on the final
product, using a Wyatt miniDAWN LS detector in 60 mW
power at a wavelength of 658 nm, and a Shodex RI-101 RI
detector uses white light as the light source with two PLgel
mixed-C columns (300ꢀ7.5 mm, 5 μm). This characterization
was performed at 40 ꢀC with THF as the mobile phase at a flow
rate of 0.8 mL/min; dn/dc was 0.128 mL/g.
Determination of Molecular Weights by TGIC. Unlike SEC,
TGIC6,7 is an interaction chromatographic technique in which
the separation is driven by enthalpic interactions between the
sample and the stationary phase. The interaction strength is
controlled by varying the column temperature7,8 and eluent com-
position,9,10 and the molecular weight resolution is little affected
by chain architecture. Therefore, TGIC is believed to be more
sensitive to the chemical nature of a polymer7-9 and to have a
higher resolution than SEC.3,11-13 The TGIC separations were
carried out using a standard high-performance liquid chroma-
tography (HPLC) system equipped with a C18 bonded silica
˚
column (Phenomenex, Kromasil, 300 A pore, 150ꢀ4.6 mm, 5 μm
particle size); the mobile phase was 1,4-dioxane at a flow rate of
0.5 mL/min, and dn/dc was 0.095 mL/g. The system was equip-
ped on line with a Wyatt miniDAWN LS detector and a Shodex
RI-101 RI detector. The column temperature profile is indicated
by solid lines in Figure 5 which were adjusted in a way to cover
the range of molar mass of each sample.
Results and Discussion
Isomeric Composition. Characteristic peaks determined by
1H NMR for the cis/trans 1,4 and 1,2 vinyl configurations
were identified,14,15 and the corresponding areas under the
peaks were calculated by the operating software. As proposed
by Tanaka et al.,15 the mole fractions of 1,2 and 1,4 units can
be calculated by eqs 1 and 2 where the bracket denotes the
mole fraction of the respective isomeric unit indicated and I(δ)
is the relative integrated intensity of the signal with chemical
shift δ. The ratio of the integrated intensity of the signal of
the trans type protons to that of the cis ones in the 2 ppm
(aliphatic) or 5 ppm (olefinic) region indicates the ratio of
trans to cis in the polymer.14,16 As noted by Santee et al., the
aliphatic region is not as distinct as the olefinic region due to
spin-spin coupling effects.14 Thus, the trans-to-cis ratio was
calculated by eq 3 using the olefinic region.
Figure 1. Synthesis steps for the anionic polymerization of H-PBD.
configurations can be resolved by use of 500 MHz field. Our
NMR studies were carried out on a 500 MHz Varian unity spec-
trometer at room temperature. A sample of 10 mg was dissolved
in 0.7 mL of deuterated chloroform (Cambridge Isotope Labo-
ratories Inc.) in 5 mm 508 Up NMR tubes. Samples were inject-
ed into the probe, shimmed, and scanned 32 times.
Determination of Molecular Weights by SEC. Molecular
weights of the H-PBDs were determined in three laboratories
under the supervision of qualified scientists. The first character-
ization (SEC-1) was performed using SEC equipped with two-
angle laser light scattering (TALLS) in 30 mW power at a
wavelength of 685 nm, a refractive index (RI) detector at a
wavelength of 680 nm, and a Viscotek differential viscometer to
determine the precursors and final products. The columns were
Waters Ultrastyragel HR series, HR-2, HR-4, HR-5E, and HR-
Ið1:3Þ
2½1, 2ꢁ
¼
ð1Þ
Ið2:0- 2:1Þ
½1, 2ꢁ þ 4½1, 4ꢁ
3
4
5
˚
6E, with pore sizes 10 , 10 , and 10 A. Measurements were done
at 40 ꢀC with tetrahydrofuran (THF) as the mobile phase at a
flow rate of 1.0 mL/min. An average value of the refractive index
increment (dn/dc) 0.130 mL/g was used in determining the molar
mass of the intermediate products. The characterization was
performed in parallel with the synthesis2 and thus provided
information on the product of each stage of the polymerization
(i.e., step 2 and step 4 in Figure 1) in addition to the final
product. “Final product” refers to the result of step 5 in Figure 1
after fractionation with toluene/methanol as the solvent/non-
solvent pair.2 The second SEC characterization (SEC-2) was
performed on the final product using a SEC system of Waters
½1, 2ꢁ þ ½1, 4ꢁ ¼ 1
ð2Þ
ð3Þ
Ið5:4Þ
Ið5:3Þ
:
Ið5:4Þ þ Ið5:3Þ Ið5:4Þ þ Ið5:3Þ
The mole fractions of cis 1,4 and trans 1,4 are then
calculated by multiplying the above ratio by the overall 1,4
content given by eq 2. Results of isomeric content are sum-
marized in Table 1, which shows that all samples had high
levels of 1,4-addition (g94%) as had been desired.