Name: 1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions (Video) | JoVE Journal
Uploaded: 2016-10-10T13:00:00.000+00:00
Duration: 6 min 56 s
Description: Learn to prepare lithium solvated electron solutions using 1,3,5-triphenylbenzene and corannulene as electron receptors. This method enables faster-charging battery technology for electric vehicles.

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5 minutes

The authors acknowledge funding from the Singapore Ministry of Education Tier 2 Research Fund (project MOE2013-T2-2-002) for this project.

1. Preparation Procedure for 1,3,5-Triphenylbenzene (1)
<ol>
	<li>Place a mixture of acetophenone (4.0 g, 33.3 mmol) and 100 ml of absolute ethanol into a round bottom three neck 250 ml flask equipped with magnetic stirrer, reflux condenser, nitrogen inlet, bubbler, dropping funnel and thermometer. Add silicon tetrachloride (11.9 g, 8.0 ml, 70.2 mmol, 2.1 eq.) to the mixture in one portion at 0 &#176;C under nitrogen using the dropping funnel.</li>
	<li>Observe the evolution of gaseous hydrogen chloride for 10 min. Then stir the reaction mixture at 40 &#176;C for 20 hr.</li>
	<li>Cool down the reaction mixture to 23 &#176;C and pour in 200 g of water mixed with ice (1:1 mass ratio).</li>
	<li>Extract the resulting mixture with dichloromethane (2 x 100 ml) using an extraction funnel.</li>
	<li>Wash the combined extracts once with saturated NaCl solution (100 ml), and dry over 15 g of anhydrous MgSO4. Filter the liquid part off and then concentrate using a rotary evaporator.</li>
	<li>Purify the product via recrystallization from ethanol (dissolution in minimal amount of ethanol followed by partial evaporation of the solvent, keeping at 6 &#176;C overnight, and rapid filtration) to obtain 2.2 g (yield 63%) of 1,3,5-triphenylbenzene (1) as pale yellow crystals. 
	Note: 1H-NMR (400 MHz, CDCl3): &#948;= 7.41 (m, 3H), 7.50 (m, 6H), 7.72 (d, 6H, J = 7.33Hz), 7.80 (s, 3H). 13C-NMR (400 MHz, CDCl3): &#948;= 125.21, 127.39, 127.57, 128.88, 141.18, 142.38.</li>
</ol>
2. LiSES Prepared with 1,3,5-Triphenylbenzene
<ol>
	<li>Preparation of 1,3,5-triphenylbenzene-based LiSES 
	NOTE: 1,3,5-triphenylbenzene used in this paper was synthesized as per procedure described above. The 1,3,5-triphenylbenzene -based LiSES are denoted by LixTPB(THF)24.7 where x denotes the Li:PAH molar ratio and TPB denotes 1,3,5-triphenylbenzene. Prepare LixTPB(THF)24.7 inside an argon-filled glovebox at ambient temperature via the following steps:
	<ol>
		<li>Measure out well defined quantities of metallic Li, THF and TPB separately inside the glovebox to achieve the target molar composition of LixTPB(THF)24.7 for x = 1, 2, 3, and 4. Use 41.6 mg, 83.3 mg, 124.9 mg, 166.6 mg of Li for x = 1, 2, 3 and 4 respectively.</li>
		<li>For each of the four LiSES samples to be prepared, dissolve 1.84 g of TPB in 12 ml of THF inside four separate glass bottles to form 12 ml of colorless solutions of TPB(THF)24.7 for each bottle. Use a 0.5 M 1,3,5-triphenylbenzene in all the solutions.</li>
		<li>Add the weighed metallic Li foils to the four bottles and seal the bottles with Parafilm.</li>
		<li>Stir the mixture in each bottle overnight using a glass-coated magnetic stirrer to ensure the complete dissolution of metallic Li.</li>
	</ol>
	</li>
	<li>Conductivity Measurements
	<ol>
		<li>Carry out all conductivity measurements using a standard conductivity cell probe based on the four-electrode technique. Attach the cell probe to a meter. The probe has a secondary function to measure the solution&#39;s temperature at the same time and display both conductivity and temperature measurements.</li>
		<li>Prior to measurements, calibrate the meter using 50 ml of standard 0.01 M aqueous KCl solution provided by the conductivity probe&#39;s manufacturer outside the glovebox.</li>
		<li>Carry out all the conductivity measurements for 1,3,5-triphenylbenzene-based LiSES, LixTPB(THF)24.7 for x = 1, 2, 3, 4 inside the glovebox.</li>
		<li>For each of these LiSES, pour out the sample into a short glass cylinder and immerse the probe into the solution. Record the conductivity measurement over a period of one to two hours till each sample returns to an ambient temperature. The time taken for each sample to return to ambient temperature is ~1-2 hr. The probe will remain immersed in the sample for the entire duration of conductivity measurement.</li>
	</ol>
	</li>
</ol>
3. Corannulene
<ol>
	<li>Preparation of corannulene-based LiSES 
	NOTE: The corannulene used in this paper was synthesized at the School of Physical and Mathematical Sciences, NTU using a multistep literature procedure.9 The corannulene-based LiSES are denoted by LixCor(THF)247 where x denotes the Li:PAH molar ratio and Cor denotes the corannulene. Prepare LixCor(THF)247 inside an argon-filled glovebox at ambient temperature via the following steps:
	<ol>
		<li>Measure out well defined quantities of metallic Li, THF and Cor separately inside the glovebox to achieve the target molar composition of LixCor(THF)247 for x = 1, 2, 3, 4 and 5. Use 4.2 mg, 8.3 mg, 12.5 mg, 16.6 mg and 20.8 mg of Li for x = 1, 2, 3, 4 and 5 respectively.</li>
		<li>Next, for each of the five LiSES samples (x = 1, 2, 3, 4 and 5) to be prepared, dissolve 0.15 g of Cor in 12 ml of THF inside five separate glass bottles to form 12 ml of colorless solution of Cor(THF)247 in each bottle. Use a corannulene concentration of 0.05 M).</li>
		<li>Next, add the weighed metallic Li foils to the five bottles of Cor(THF)247 and seal the bottles with Parafilm.</li>
		<li>Stir the mixture in each bottle overnight using a glass-coated magnetic stirrer to ensure the complete dissolution of the metallic lithium.</li>
	</ol>
	</li>
	<li>Conductivity Measurements
	<ol>
		<li>For conductivity versus temperature measurements, remove each of the five bottles containing LixCor(THF)247 for x = 1, 2, 3, 4 and 5 individually from the glovebox, wrap it with an additional layer of para-film and immerse it inside an insulated Styrofoam container filled with dry ice. 
		NOTE: The LiSES samples did not come into contact with either moisture or oxygen while outside the glovebox because the bottles were sealed.</li>
		<li>Cool each bottle down to about 10 &#176;C by keeping each bottle immersed in the dry ice for about 30 min before being transferred back into the glovebox for conductivity measurements.</li>
		<li>Purge the ante-chamber of the glovebox at least 5 times for each cooled sample to ensure that no traces of water of condensation accompany the bottle back into the glovebox.</li>
		<li>Similar to the manner in which conductivity versus temperature measurements were collected for naphthalene-based LiSES samples1, measure the conductivity of LixCor(THF)247 (x = 1, 2, 3, 4, 5) over a period of one to two hours till each sample returned to ambient temperature. The probe will remain immersed in the sample for the entire duration of conductivity measurement.</li>
	</ol>
	</li>
</ol>

<ol><li>Tan, K. S., Yazami, R. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((Physical-Chemical+and+Electrochemical+Studies+of+the+Lithium+Naphthalenide+Anolyte%5BTitle%5D)+AND+%22Electrochim+Acta%22%5BJournal%5D)">Physical-Chemical and Electrochemical Studies of the Lithium Naphthalenide Anolyte.</a> Electrochim Acta. 180, 629-635 (2015).</li>
<li>Tan, K. S., Grimsdale, A. C., Yazami, R. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((Synthesis+and+Characterisation+of+Biphenyl-Based+Lithium+Solvated+Electrons+Solutions%5BTitle%5D)+AND+%22J+Phys+Chem+B%22%5BJournal%5D)">Synthesis and Characterisation of Biphenyl-Based Lithium Solvated Electrons Solutions.</a> J Phys Chem B. 116, 9056-9060 (2012).</li>
<li>Rinaldi, A., Tan, K. S., Wijaya, O., Wang, Y., Yazami, R. Ch. 11. <a target="_blank" href="http://scholar.google.com/scholar?hl=en&safe=off&q=author%3aRinaldi%2C+A+%22Advances+in+batteries+for+large-+and+medium-scale+energy+storage+applications+in+power+systems+and+electric+vehicles%22">Advances in batteries for large- and medium-scale energy storage applications in power systems and electric vehicles</a>. Menictas, C., Skyllas-Kazacos, M., Lim, T. M., Hughes, S. , Woodhead Publishing Ltd. (2014).</li>
<li>Wang, Y., Tan, K. S., Yazami, R. <a target="_blank" href="http://scholar.google.com/scholar?hl=en&safe=off&q=author%3aWang%2C+Y+%22Materials+Challenges+In+Alternative+%26+Renewable+Energy+%28MCARE+2014%29%22">Materials Challenges In Alternative & Renewable Energy (MCARE 2014)</a>. , Florida, USA. (2014).</li>
<li>Yazami, R., Tan, K. S. <a target="_blank" href="http://scholar.google.com/scholar?hl=en&safe=off&q=author%3aYazami%2C+R+%22in+8th+annual+Li+Battery+Power%22">in 8th annual Li Battery Power</a>. , Boston, USA. (2012).</li>
<li>Hybrid Electrochemical Generator With A Soluble Anode. US patent. , 20100141211A1 (2010).</li>
<li>Yazami, R., Tan, K. S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((Liquid+Metal+Battery%5BTitle%5D)+AND+%22US+patent%22%5BJournal%5D)">Liquid Metal Battery.</a> US patent. , 20150333353A1 (2015).</li>
<li>Lim, Z. B., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((Synthesis+and+assessment+of+new+cyclopenta-2%2C4-dienone+derivatives+for+energy+storage+applications%5BTitle%5D)+AND+%22Synthetic+Met%22%5BJournal%5D)">Synthesis and assessment of new cyclopenta-2,4-dienone derivatives for energy storage applications.</a> Synthetic Met. 200, 85-90 (2015).</li>
<li>Butterfield, A. M., Gilomen, B., Siegel, J. S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((Kilogram-Scale+Production+of+Corannulene%5BTitle%5D)+AND+%22Org.+Process+Res.+Dev%22%5BJournal%5D)">Kilogram-Scale Production of Corannulene.</a> Org. Process Res. Dev. 16, 664-676 (2012).</li>
<li>Elmorsy, S. S., Pelter, A., Smith, K. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((The+direct+production+of+tri-+and+hexa-substituted+benzenes+from+ketones+under+mild+conditions%5BTitle%5D)+AND+%22Tetrahedron+Lett%22%5BJournal%5D)">The direct production of tri- and hexa-substituted benzenes from ketones under mild conditions.</a> Tetrahedron Lett. 32, 4175-4176 (1991).</li>
<li>Zabula, A. V., Filatov, A. S., Spisak, S. N., Rogachev, A. Y., Petrukhina, M. A. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/pubmed?term=((A+Main+Group+Metal+Sandwich%3A+Five+Lithium+Cations+Jammed+Between+Two+Corannulene+Tetraanion+Decks%5BTitle%5D)+AND+%22Science%22%5BJournal%5D)">A Main Group Metal Sandwich: Five Lithium Cations Jammed Between Two Corannulene Tetraanion Decks.</a> Science. 333, 1008-1011 (2011).</li>
</ol>

The authors have nothing to disclose.

For the 1,3,5-triphenylbenzene-based LiSES, a sample with a light color shows that it has a low concentration of solvated electrons. LixTPB(THF)24.7 (for x = 1, 2, 3, 4) demonstrates a behavior in its conductivity versus x similar to that seen for LiSES made from biphenyl and naphthalene1, 2.There is an initial increase in conductivity with increase of Li:PAH ratio from 1 to 2 and a subsequent decrease in conductivity upon further increasing the molar ratio to 3 and 4, with condu...

Lithium solvated electron solutions (LiSES) prepared using simple two-ring polyaromatic hydrocarbons (PAH) such as biphenyl and naphthalene can potentially be utilized as liquid anodes in refuelable lithium cells1-7. In the LiSES, these simple PAH molecules served as the electron receptors for solvated electrons from dissolved metallic lithium.
Progressing from these two-ring systems, the authors have since then carried out conductivity measurement studies on LiSES which are prepared using more complex PAHs, starting with the group of cyclopenta-2,4-dienone derivatives8. These PAHs include larger PAHs (&gt;two benzene rings) and PAHs with substituents incorporated into their aromatic rings. A larger PAH molecule with more than two rings is expected to accommodate more lithium atoms per PAH molecule than either biphenyl or naphthalene thus resulting in LiSES with a higher energy density. The objective of introducing substituents into PAHs is to make the PAH accept electrons more readily and become more stable as polyanions in LiSES.
As part of ongoing efforts to develop LiSES with higher energy density, this paper will report on the characterization of LiSES prepared from corannulene made by the literature procedure9 as well as 1,3,5-triphenylbenzene, TPB synthesized by a slightly modified literature 10. 1,3,5-triphenylbenzene, as shown in Figure 1(1), can be classified as a biphenyl derivative with two additional phenyl rings at positions 3 and 5 of the same ring. Since this molecule has four benzene rings, it should uptake 4 atoms of Li per molecule, which is more than for biphenyl (maximum 2.5 mole equivalents of Li per PAH in 0.5 M solution) and naphthalene (&lt;2.5 mole equivalents of lithium per molecule).
Corannulene is a five-ring PAH arranged into a bowl shape as shown in Figure 1(2). Zabula et al.11 have demonstrated the feasibility of dissolving metallic lithium in a solution of corannulene/tetrahydrofuran (THF) to form a solution with five Li+ ions sandwiched between two stable tetraanions of corannulene.
<img alt="Chemical structure diagram of 1,3,5-triphenylbenzene and corannulene." src="/files/ftp_upload/54366/54366fig1.jpg" data-altupdatedat="1788235205000" data-alt="Figure 1"> 
Figure 1: The molecular structures of 1,3,5-triphenylbenzene (1) and corannulene (2). 1,3,5-triphenylbenzene is classified as a biphenyl derivative with two additional phenyl rings at positions 3 and 5 of the same ring. Corannulene is a five-ring PAH with its five benzene rings arranged into a bowl shape. <a href="https://www.jove.com/files/ftp_upload/54366/54366fig1large.jpg" target="_blank">Please click here to view a larger version of this figure.</a>
Thus, both 1,3,5-triphenylbenzene and corannulene are potential candidates for high energy density LiSES.

<table><tbody><tr><td>Tetrahydrofuran Anhydrous, &amp;#8805;99.9%, Inhibitor-free</td><td>Sigma Aldrich</td><td>401757-100ML</td><td></td></tr><tr><td>Lithium Foil&amp;nbsp;</td><td>Alfa Aesar</td><td>010769.14</td><td></td></tr><tr><td>Cond 3310 Conductivity Meter</td><td>WTW</td><td>Not Applicable</td><td></td></tr><tr><td>1,3,5-triphenylbenzene</td><td></td><td></td><td>Synthesized from acetophenone according to procedure described in literature</td></tr><tr><td>Silicon tetrachloride</td><td>Sigma Aldrich</td><td>215120-100G</td><td></td></tr><tr><td>acetophenone</td><td>TCI</td><td>A0061-500g</td><td></td></tr><tr><td>Ethanol</td><td>Merck Millipore</td><td>1.00983.2511</td><td></td></tr><tr><td>Corannulene</td><td></td><td></td><td>Synthesized by literature procedure</td></tr></tbody></table>

1,3,5-triphenylbenzene and corannulene as electron receptors for lithium solvated electron solutions

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

The authors report on conductivity studies carried out on lithium solvated electron solutions (LiSES) prepared using two types of polyaromatic hydrocarbons (PAH), namely 1,3,5-triphenylbenzene and corannulene, as electron receptors. The solid PAHs were first dissolved in tetrahydrofuran (THF) to form a solution. Metallic lithium was then dissolved into these PAH/THF solutions to yield either blue or greenish blue solutions, colors which are indicative of the presence of solvated electrons. Conductivity measurements at ambient temperature carried out on 1,3,5-triphenylbenzene-based LiSES, denoted by LixTPB(THF)24.7 (x = 1, 2, 3, 4), showed an increase of conductivity with increase of Li:PAH ratio from x = 1 to 2. However, the conductivity gradually decreased upon further increasing the ratio. Indeed the conductivity of LixTPB(THF)24.7 for x = 4 is even lower than for x = 1. Such behavior is similar to that of the previously reported LiSES prepared from biphenyl and naphthalene. Conductivity versus temperature measurements on corannulene-based LiSES, denoted by LixCor(THF)247 (x = 1, 2, 3, 4, 5), showed linear relationships with negative slopes, indicating a metallic behavior similar to biphenyl and naphthalene-based LiSES.

Reaction between various amounts of lithium and mixtures of 1,3,5-triphenylbenzene with THF gives greenish blue or deep blue colored solutions as shown in Figure 2. A light color indicates that the particular sample of LiSES has a low concentration of solvated electrons. 1,3,5-triphenylbenzene demonstrates increase of conductivity with increase of Li:PAH ratio from 1 to 2 in 0.5 M THF solution (Table 1). However, conductivity value gradually decreases upon further increasing the molar ra...

The authors report on conductivity studies carried out on lithium solvated electron solutions (LiSES) prepared using 1,3,5-triphenylbenzene (TPB) and corannulene as electron receptors.

The authors report on conductivity studies carried out on lithium solvated electron solutions (LiSES) prepared using two types of polyaromatic ...

The overall goal of this experiment is to show the preparation method of LISES and to measure some of their physical chemical properties in view of their application in rechargeable batteries. This method can help answer key questions in the physical chemistry field about the preparation and physical properties of lithium sulfated argon solutions. The main advantage of this technique is that it provides an inert material in the liquid state at ambient temperature.The implications of this technique extend toward next generation refillable lithium batteries for electric vehicles. Currently some ion batteries require overnight charging, whereas refillable batteries may be recharged in ten minutes. Visual demonstration of this method is critical as the steps to make the LISES need to be repeated exactly for the best results and to avoid potential hazards.The synthesis will be demonstrated by Andrew Lunchev, a PhD student in the group of professor Andrew Grimsdale. Place four grams of acetophenone in 100 milliliters of absolute ethanol in a triple neck 250 milliliter round bottom flask, equipped with a magnetic stir bar, reflux condenser, dropping funnel, gas bubbler, nitrogen inlet and thermometer. Place the reaction mixture under a nitrogen atmosphere.Then cool the mixture to zero degrees Celsius. Using the dropping funnel, add 2.1 equivalents of silicon tetrachloride to the mixture in a single portion. Monitor the reaction mixture for ten minutes, during which gaseous hydrogen chloride will form.Then heat the mixture to 40 degrees Celsius while stirring and continue stirring for 20 hours. Then cool the reaction mixture to room temperature and add ice water in a 1:1 mass ratio with the reaction mixture. Extract twice with dichloromethane.Combine the extracts and wash them with 100 milliliters of saturated sodium chloride solution. Then dry the mixture of anhydrous magnesium sulfate. Filter the mixture to remove the magnesium sulfate and concentrate the filtrate with a rotary evaporator.Recrystalization from ethanol yields 1, 3, 5-triphenlybenzene. Perform all preparation of the litium sulfated electron solutions in an argon filled glovebox. First place 12 milliliters of tetrahydrofuran in each of nine glass vials.Then dissolve six millimoles of TPB in each of four of the vials to form a 0.5 molar solution. To each of the remaining five vials add 0.6 millimoles of corannulene to form a 0.05 molar solution. To prepare TPB based LISES with lithium TPB molar ratios ranging from one to four, add six, 12, 18 and 24 millimoles of metallic lithium to the four vials of TPB solution Then, to prepare core based LISES with lithium core molar ratios ranging from one to five, add 0.6, 1.2, 1.8, 2.4, and 3 millimoles of metallic lithium to the five vials of core solution.Add a borosilicate glass-coated magnetic stir bar to each of the vials, close the vials and seal the vials with laboratory film. Stir all mixtures overnight to completely dissolve the metallic lithium. Perform the procedure in a glovebox with a calibrated conductivity meter capable of measuring solution temperature Immediately before measuring the conductivity of the LISES samples, remove each tightly sealed sample from the glovebox.Wrap the vial in an additional layer of laboratory film and cool the sample to approximately 10 degrees Celsius. Do not allow the sample to freeze solid. Transfer the cooled sample back into the glovebox, purging the antichamber at least five times to exclude moisture from condensation.Record conductivity measurements for each sample until the sample returns to room temperature. Keeping the probe immersed in the solution throughout. Plotting conductivity of the corannulene-based LISES against temperature reveals a linear relationship with a negative slope, indicating metallic conductivity behavior.Using this relationship the temperature coefficient and the conductivity at ambient temperature can be determined for each lithium-corannulene molar ratio tested. The conductivity of 135-triphenlybenzene based LISES increases when the lithium to TPB ratio increases from one to two. The conductivity then decreases as the ratio continues to increase.Previously studied naphthalene and biphenyl based LISES demonstrates similar metallic conductivity behavior and changes in conductivity with changing molar ratios. Once mastered, this technique can be done in one hour if it is performed properly. Well attempting this procedure it is important to remember to always prepare an LISES in a controlled, dry environment, such as in an argon filled glovebox and to never expose an LISES to the ambient atmosphere.Following this procedure, other methods like preparing a liquid cathode can be performed in order to answer additional questions about the concept of liquid anode and liquid cathode lithium cell.

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Learn to prepare lithium solvated electron solutions using 1,3,5-triphenylbenzene and corannulene as electron receptors. This method enables faster-charging battery technology for electric vehicles.

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

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