Enlarged Tetrasubstituted Alkenes With Enhanced Thermal and Optoelectronic Properties

Figure S6. High resolution mass spectrum of 2TDFE. Figure S7. The TEM images and electron diffraction patterns of (A) 2ADFE and (B) 2TDFE formed in THF/water mixtures with 95% water fractions. Figure S8. Excitation spectra of 2ADFE (left) and 2TDFE (right) in pure THF solution, in aqueous suspensions and in the solid state, respectively. Figure S9. UV-vis absorption spectra of 2ADFE in THF/water mixtures with different water fractions. Figure S10. Decay lifetime curves of 2ADFE (left) and 2TDFE (right) in pure THF solution, aqueous suspensions and the solid state.


Materials and Instrumentations
THF was distilled from sodium benzophenone ketyl under nitrogen immediately prior to use.All the chemicals and other regents were purchased from Aldrich and used as received without further purification.
1 H and 13 C NMR spectra were measured on a Bruker AV 400 spectrometer in CDCl 3 or CD 2 Cl 2 using tetramethylsilane (TMS; δ = 0) as internal reference.
Photoluminescence spectra were recorded on a Perkin-Elmer LS 55 spectrofluorometer.The fluorescence lifetime measurement was performed on the Edinburgh FLS920 spectrofluorimeter with a hydrogen flash lamp as the excitation source on the same spectrofluorometer.High resolution mass spectrum (HRMS) was recorded on a GCT premier CAB048 mass spectrometer operating in MALDI-TOF mode.Thermogravimetric analysis (TGA) was carried on a TA TGA Q5500 under dry nitrogen at a heating rate of 20 o C/min.Thermal transitions were investigated by differential scanning calorimetry (DSC) using a TA DSC Q1000 under dry nitrogen at a heating rate of 10 o C/min.Cyclic voltammogram was recorded on a Princeton Applied Research (model 273A) at room temperature.The working and reference electrodes were glassy carbon and Ag/AgNO 3 (0.1 M in acetonitrile), respectively.All the solutions were deactivated by bubbling nitrogen gas for a few minutes prior to electrochemical measurements.The oxidation potential of ferrocene was measured to be 0.05 eV, and the onset oxidation potential of 2ADFE was found at 0.52 eV (Figure S14).The formula used to estimate the HOMO level is as follows: For 2ADFEE, the HOMO = -e (0.52 + 4.8-0.05)V≈ -5.3 eV.L emission is the luminescence emission spectrum of the sample, collected using the sphere; E reflector is the spectrum of the light used for excitation with only the standard reference reflector in the sphere, collected using the sphere; E sample is the spectrum of the light used to excite the sample, collected using the sphere.
During a typical measurement procedure, the complete emission spectrum of the sample (Sample Emission, L emission ), the spectra of the excitation light recorded with the sample in place (Sample Scatter, E sample ) and the spectra of the excitation light recorded with the standard reference reflector in place (Reference Scatter, E reflector ) are measured one by one.After combination of these individual spectra, the software will calculate the fluorescence quantum yield.The instrument is calibrated by using standard Alq 3 (Tris(8-hydroxyquinolinato)aluminium) film before formal measurement.

Figure S7 .
Figure S7.The TEM images and electron diffraction patterns of (A) 2ADFE and (B) 2TDFE formed in THF/water mixtures with 95% water fractions.

Figure S8 .
Figure S8.Excitation spectra of 2ADFE (left) and 2TDFE (right) in pure THF solution, in aqueous suspensions and in the solid state, respectively.

Figure S9 .
Figure S9.UV-vis absorption spectra of 2ADFE in THF/water mixtures with different water fractions.

Figure S10 .
Figure S10.Decay lifetime curves of 2ADFE (left) and 2TDFE (right) in pure THF solution, aqueous suspensions and the solid state.

Figure. S12 .
Figure.S12.DSC thermograms of 2ADFE (A) and 2TDFE (B) recorded at a heating rate of 10 oC/min.(the second heating and cooling cycle).

Figure S13 .
Figure S13.Optimized geometries and molecular orbital amplitude plots of HOMO and LUMO energy levels of 2ADFE and 2TDFE.

Figure S15 .
Figure S15.Energy level diagrams and device configurations of multilayer EL devices of 2ADFE with and without hole-transporting layers.

For
photons emitted divided by the number of photons absorbed by a sample.The number of photons absorbed by a bulk sample is equal to the number of photons incident on the sample minus the photons passing through and not being absorbed by it.Thus the quantum yield can be represented simply in the equation below:

Scheme 1
photons emitted from the devices were detected by a calibrated UDT PIN-25D silicon photodiode.The luminance and external quantum efficiencies of the devices were inferred from the photocurrent of the photodiode.The electroluminescence (EL) spectra were obtained with the PR650 spectrophotometer.All the measurements were carried out under air at room temperature without device encapsulation.

Figure S10 .
Figure S10.Decay lifetime curves of 2ADFE (left) and 2TDFE (right) in pure THF solution, aqueous suspensions and the solid state.

Table S1
EL performances of devices based on 2ADFE and 2TDFE.

Table S1
EL performances of devices based on 2ADFE and 2TDFE.a