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Firefly-like Water Splitting Cells Based on FRET Phenomena with Ultrahigh Performance over 12% Yi-Sheng Lai, Fei Pan, and Yen Hsun Su ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.7b18003 • Publication Date (Web): 16 Jan 2018 Downloaded from http://pubs.acs.org on January 16, 2018

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ACS Applied Materials & Interfaces

Firefly-like

Water

Splitting

Cells

Based

on

FRET

Phenomena with Ultrahigh Performance over 12% Yi-Sheng Laia, Fei Panb,c, Yen-Hsun Su* a,*

Department of Materials Science and Engineering, National Cheng Kung

University, Tainan 70101, Taiwan b

Physics Department, Ludwig-Maximilians-Universität München, Schellingstrasse 4,

München 80333, Germany; c

Physics Department, Technische Universität München, James-Franck-Straße 1,

Garching 85748, Germany.

*

[email protected]

b,c

[email protected]

Keyword: ZrO2, water splitting, chlorophyll, firefly, FRET

1

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Abstract Firefly-like chemiluminescence reaction was utilized in the ZrO2 nanoparticles matrix water splitting cells, where the chlorophyll of Lantana camara was the major photosensitizer to excite electrons to the conduction band of ZrO2. The fluorescence resonance energy transfer (FRET) was induced by Rubrene, a firefly-like chemiluminescence molecule, and Lantana camara chlorophyll combined with 9,10-diphenylanthracene. The ZrO2 nanoparticles film coated by the chlorophyll of Lantana camara and 9,10-diphenylanthracene under chemiluminescence irradiation in 1 M KHCO3 water solution demonstrated the highest photocurrent density (88.1 A/m2) and the highest water splitting efficiency (12.77%).

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Introduction The light from fireflies is generated from the molecule named Luciferase1. In recent research, the extraordinary molecules with high energy transfer have been used in electrochemical devices.2-5 Shinya Yamasaki et al. controlled the bioluminescence of the bacteria by blocking the adsorption of Luciferase with electrochemical ways, moreover they proved that Luciferase had specific electrochemical stability.6 Ya-Jun Liu et al. found that the molecule with Luciferase structure could achieve over 43% quantum yield of the light emitter by calculating the energetic, charge transfer, electronic structures, and molecular dynamics by using reliable density functional theory (DFT) and time-dependent DFT principles.2 A multicolor organic light emitting device (OLED) assembled by amino oxyluciferin was developed by Chun-Gang Min et al..7 The bioluminescence reaction from fireflies is shown in Figure 1.2 In the reaction, adenosine triphosphate (ATP) reacted with Luciferin and then formed the Luciferin-AMP8. When the oxygen gas reacted with Luciferin-AMP, Luciferin-AMP would be decomposed with the generation of intermediates. The generated light was from the decomposition of the intermediates into carbon dioxide and Luciferin-keton. During the bioluminescence reaction, energy was transferred by ATP into Luciferin for the light generation without energy loss. The fantastic reaction was used in the 3



glow stick which invented by human beings.9-14 Rubrene and 9,10-diphenylanthracene were the common molecules applied in organic light emission diodes(OLEDs) and glow sticks. The quantum efficiency of Rubrene11-12,

14-19

than Luciferin.1,

and 9,10-diphenylanthracene were much higher and more stable 15, 19-24

From the mechanism of the chemiluminescence, the

derivatives of diphenyl oxalate were the limitation to exciting the Rubrene and 9,10-diphenylanthracene. The chemiluminescence was able to keep stable light for more than 10 hours with sufficient amount of the derivatives (diphenyl oxalate). The chemiluminescence reaction of Rubrene and 9,10-diphenylanthracene obeyed the mechanism shown in Figure 2, where TCPO was ruptured by H2O2 to form 1,2-dioxetanedione. Later on, 1,2-dioxetanedione would decompose to generate biradical, which subsequently excited Rubrene and 9,10-diphenylanthracene. The photons were emitted by the excited Rubrene and 9,10-diphenylanthracene and at the same time Rubrene and 9,10-diphenylanthracene returned to the ground state. For the preparation of ZrO2 films, a water splitting solar cell with ultra-wide band gap25-32, the photosensitizers absorbed the incident light to pump electrons to the conduction band of ZrO2 necessarily.33-36 The Lantana camara is an easy plant to grow with promising applications in biofuels.37-40 The chlorophyll from natural plants with suitable excitation is an excellent candidate to act as the photosensitizer in ZrO2 water 4


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splitting solar cells. As the Rubrene and 9,10-diphenylanthracene provided the Luciferase-like with high energy transfer efficiency, the Förster resonance energy transfer (FRET) was probable to increase the water splitting efficiency.3, 41-50 Ioannis Papakonstantinou et al. used the so-called luminescent solar concentrator (LSC) solution to concentrate light without any tracking device and transferred energy from two types of fluoropgores via FRET to improve the efficiency of dye sensitive solar cells (DSSC), with at least 24.7% enhancement of the optical efficiency.3 Yuegang Zhang et al. explored acceptor dyes like graphene quantum dots (GQDs) as energy relay antennas and designed donor materials in FRET based DSSCs, achieving GQDs co-sensitized DSSC with high efficiency over 7.9%.41 The photonic processes for energy production and storage Emmanuel Stratakis et al and Zhaosheng Li et al also provide photovoltaic and energystorage systems about the photochemical51-52. Emmanuel Stratakis1 and Emmanuel Kymakis provide the nanoparticle-based plasmonic organic photovoltaic devices, the photoelectro conversion efficiency is only 9.2%53. The following missions were achieved in this article: (1) ZrO2 is the best candidate for water splitting solar cells. (2) The Lantana camara chlorophyll can act as the photosensitizer to pump electrons to the conduction band of ZrO2. (3) The mechanism of firefly-like chemiluminescence and FRET can be applied in water 5



splitting cells.

6


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Experiment section Material and preparation ZrO2 nanoparticles and zirconium dichloride oxide (ZrOCl2 · 8H2O) were purchased from Sigma-Aldrich. Rubrene and 9,10-diphenylanthracene were purchased from Acros Organic. Bis(2,4,6-trichlorophenyl) oxalate (TCPO) and Tetrabutylammonium Perchlorate (TBAP) were purchased from Tokyo Chemical Industry (TCI). Toluene (Solvents for Gas Chromatography) and ethanol were purchased from Merck Chemicals. Potassium bicarbonate (KHCO3) and hydrogen peroxide 35% (H2O2) were purchased from Showa Chemical Industry. Platinum foil (0.25 mm thick) were purchased from Alfa Aesar. Lantana camara (LC) leaves were the resource of the nature chlorophyll. 1 kg Air-dried Lantana camara leaves were soaked in 1000 ml ethanol to prepare the chlorophyll solution. The chlorophyll solution was evaporated by 950 ml solvent and then concentrated by the rotary evaporator. The ZrO2 nanoparticles films were prepared from ZrO2 nanoparticles suspension solution and zirconium dichloride oxide solution. 0.3 g ZrO2 nanoparticles were dispersed into 10 ml ethanol for the preparation of the ZrO2 nanoparticles suspension solution. 0.5 g Zirconium dichloride oxide was dissolved into 10 ml ethanol to prepare the zirconium dichloride oxide solution. 1 ml/cm2 ZrO2 nanoparticles 7



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suspension solution was dipped on the pre-cleaned indium tin oxide (ITO) glass. As the ZrO2 nanoparticles films were dried in air, 1 ml/cm2 zirconium dichloride oxide solution was dipped on the dried ZrO2 nanoparticles films before backing under 150 ℃ for 12 hr. The electrode of the cells was prepared by the ZrO2 nanoparticles coated by the Lantana

camara

chlorophyll/Rubrene

and

the

Lantana

camara

chlorophyll/9,10-diphenylanthracene respectively. The coated Lantana camara chlorophyll on the ZrO2 nanoparticles film served as the

major

photosensitizer

9,10-diphenylanthraceneand/TCPO

agent.

Then,

Rubrene/TCPO

and

were coated on ZrO2 nanoparticles films with

the Lantana camara chlorophyll. The employed chemiluminescence reaction system followed with the addition of Rubrene/TCPO and 9,10-diphenylanthracene/TCPO of the molar ratio of 1:1, respectively. The Pt foil (1 cm2) served as the counter electrode. The employed electrolytes for obtaining water splitting reactions was 1 M KHCO3 water solution (per 100 ml solution contained 20 ml ethanol and 80 ml H2O2 solution). Characterization Particle size and morphology of the ZrO2 were investigated by high resolution 8


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scanning electron microscopy with field emission (HR-FE-SEM). Observation was carried out using a field emission scanning electron microscopy, Hitachi 6700F microscope. The powder X-ray diffraction (XRD) patterns were recorded and tested by German Bruker AXS (D8) X-ray diffractometer with Cu Kα radiation. The wavelength, λ is 1.5418 Å, accelerated voltage is 40 kV, current is 40 mA with a scanning speed of 0.10° min-1 in 10~70°. Optical analysis was carried out with a CT-2200 spectrophotometer, where the quartz cell was applied in the measurement and the light path was about 1 cm. The emission intensity of the chemiluminescence reaction from Rubrene and 9,10-diphenylanthracene was measured by the integrating sphere which was from Gamma Scientific (GS-IS1 with Barium-Sulfate coating) and recorded by Spectra Suite (Ocean Optics). The current density of the water splitting cells were performanced by a CH Instruments (6273E) to carry out the experiments of hydrogen generation.

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Result and Discussion Optical Characteristic For investigating the optical characteristics, the UV-vis spectrum of Lantana camara chlorophyll, Rubrene and 9,10-diphenylanthracene are shown in Fig 3. The chlorophyll, extracted from Lantana camara leaf, has high absorption intensity when the wavelength range is below 500 nm. Rubrene shows the strongest absorption peak at 300 nm and a minor absorption intensity during the wavelength range 600 nm - 400 nm. 9,10-diphenylanthracene demonstrates a huge absorption intensity at the wavelength below 430 nm. The photoluminescence (PL) spectrum of the Lantana camara chlorophyll, Rubrene and 9,10-diphenylanthracene are shown in Figure 4. The maximum emission intensity peaks are 630 nm for Rubrene, 460 nm for 9,10-diphenylanthracene and 790 nm for Lantana camara chlorophyll. As

the

ZrO2

nanoparticles

films

are

coated

with

Lantana

camara

chlorophyll/Rubrene and Lantana camara chlorophyll/9,10-diphenylanthracene, the PL spectrum of Lantana camara chlorophyll/Rubrene and Lantana camara chlorophyll/9,10-diphenylanthracene are measured and shown in Figure 5 respectively. The Lantana camara chlorophyll/Rubrene in Figure 5a is marked as LCR, which shows the highest emission intensity peak at 790 nm and the lowest emission intensity 10


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peak at 630 nm. The Lantana camara chlorophyll/9,10-diphenylanthracene in Figure 5b is marked as LCDPA, which shown the highest emission intensity peak at 790 nm and the lowest emission intensity peak at 460 nm. There is a typical fluorescence resonance energy transfer (FRET) phenomena shown in Figure 5, where there is decrease of the PL emission intensity of Rubrene and 9,10-diphenylanthracene and increase of the emission intensity of the LC chlorophyll. Thus, at the condition of Lantana camara chlorophyll/Rubrene and the Lantana camara chlorophyll/9,10-diphenylanthracene mixture, Lantana camara chlorophyll acts as the acceptor molecule, and Rubrene and 9,10-diphenylanthracene serve as the donor molecules. Current density and the water splitting efficiency The current density-voltage (J-V) characteristic curves are recorded and analyzed by a CH Instrument from the water splitting cells of the ZrO2 nanoparticles films coated with Lantana camara chlorophyll/Rubrene and Lantana camara chlorophyll/9,10-diphenylanthracene under chemiluminescence irradiation within 1 M KHCO3 water solution electrolyte. The water splitting cells are operated under chemiluminescence irradiation and applied negative voltages conditions to carry out the efficient hydrogen generation. The circuit of the water splitting cells by applying negative voltages is shown 11



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in Figure 6. At first, Rubrene and 9,10-diphenylanthracene emit the light to Lantana camara chlorophyll by chemiluminescence reaction and then Lantana camara chlorophyll absorbs the light from Rubrene or 9,10-diphenylanthracene and generates the excited electrons. Since negative voltages were applied in the water splitting experiments, the excited electrons transport into the electrolyte to reduce H+ ions into hydrogen gas directly. Thus, Pt foil transports the electron holes into the electrolyte to oxidize OH- ions into oxygen gas. The current density and the water splitting efficiency has been investigated for the ZrO2 nanoparticles films coated by the Lantana camara chlorophyll/Rubrene and

the

Lantana

camara

chlorophyll/9,10-diphenylanthracene

under

chemiluminescence irradiation within 1 M KHCO3 solution as electrolyte. The efficiency calculation is following the equation (1).

(1) where the photocurrent density at Eop is Jop, and Eop is the applied voltage under optimal conditions. The input energy Int is the simulations solar light AM 1.5 G (1000 W/m2). The light source is applied in our water splitting experiments concerning the chemiluminescence, therefore, the light from the chemiluminescence is transferred at the same order compared with transfer of light by optical integrating sphere, where the lowest applied voltage for electrolyzing water into O2 and H2 is 12


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1.23 V. Applying negative voltages, the photocurrent density of ZrO2 nanoparticles films coated by the organic pigments in 1 M KHCO3 water solution under chemiluminescence irradiation is shown in Figure 7 and the results in detail are listed in Table 1. As shown in Figure 7a, the ZrO2 nanoparticles films coated with Lantana camara chlorophyll/9,10-diphenylanthracene have the highest photocurrent density (88.1 A/m2). From the Figure 7b and Table 1, 20 ml/cm2 hydrogen gas is generated by ZrO2

nanoparticles

films

coated

with

Lantana

camara

chlorophyll/9,10-diphenylanthracene in a time span of 1800 s and the water splitting efficiency of ZrO2 nanoparticles films coated with LCDPA is 12.77%. The emitted light from DPA is totally absorbed by Lantana camara chlorophyll only when the FRET mechanism can be applied. According to Figure 5, the PL intensity of Lantana camara chlorophyll is enhanced by 9,10-diphenylanthracene slightly which means the light energy from 9,10-diphenylanthracene transferred to Lantana camara chlorophyll and contributed to water splitting. Thus, the water splitting efficiency of ZrO2 nanoparticles films coated with Lantana camara chlorophyll and 9,10-diphenylanthracene shows the highest efficiency and current density. As the water splitting cells utilize the firefly-like chemiluminescence irradiation and the FRET mechanism, the water splitting efficiency is achieved up to 13



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12.77%. The relate water splitting cells researches is listed for comparison.

Leanne G.

Bloor et al. utilized phosphomolybdate ([PMo12O40]3−) matrix in water splitting system and presented that the highest photocurrent density is 2.5 mA/cm2 (25 A/m2) and the efficiency is only 2%54. Jianping Lai et al. presented the water splitting solar cell prepared by nitrogen, phosphorus and oxygen tri-doped porous graphite carbon@oxidized carbon cloth (ONPPGC/OCC). The current density at 1.66 V applied voltage is 10 mA/cm2 (100 A/m2)55. Jinhui Yang et al. prepared the water splitting cell by Co3O4/Co(OH)2 thin films. The current density is almost zero when the cell voltage is lower than 1.23 V at the working temperature > 100℃26. After the comparison of all cells, firefly-like water splitting cells presents the highest photocurrent density and the highest water splitting efficiency.

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Conclusion Firefly-like chemiluminescence and FRET mechanism are successfully applied in water splitting cells with high performance. 9,10-diphenylanthracene shows the firefly-like

chemiluminescence

reaction

and

Lantana

camara

chlorophyll/

9,10-diphenylanthracene demonstrate fluorescence resonance energy transfer (FRET) phenomena.

ZrO2

nanoparticles

films

coated

with

Lantana

camara

chlorophyll/9,10-diphenylanthracene in the 1 M KHCO3 water solution under chemiluminescence irradiation and applied negative voltages provide the highest photocurrent density (88.1 A/m2), the highest water splitting efficiency (12.77 %) and over 20 ml hydrogen gas (per 1 cm2 in 1800 s).

15



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Figure Legends. Figure 1. The mechanism of the chemiluminescence reaction by the firefly Luciferin.

Figure 2. The mechanism of the chemiluminescence reaction by a glow stick.

Figure 3. Absorption spectra of the pigments. LC: the Lantana camara chlorophyll, R: Rubrene and DPA: 9,10-diphenylanthracene.

Figure 4. Photoluminescence spectra of the pigments. LC: the Lantana camara chlorophyll, R: Rubrene and DPA: 9,10-diphenylanthracene.

Figure 5. Photoluminescence spectrum of the pigment with the FRET phenomena. (a) Lantana

camara

chlorophyll/Rubrene

solution

and

(b)

Lantana

camara

chlorophyll/9,10-diphenylanthracene solution. (LC: the Lantana camara chlorophyll, R:

Rubrene,

DPA:

chlorophyll/Rubrene

9,10-diphenylanthracene, solution

and

LCR:

LCDPA:

Lantana Lantana

camara camara

chlorophyll/9,10-diphenylanthracene solution).

Figure 6. The water splitting cells with firefly-like chemiluminescence irradiation by 16


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applying negative voltages.

Figure 7. (a) The current density of the water splitting cell by chemiluminescence irradiation and negative voltages in the electrolyte of 1 M KHCO3 water solution; (b) Hydrogen generation from the water splitting cell. (LC coated with the Lantana camara chlorophyll, LCR coated with the Lantana camara chlorophyll/Rubrene, and LCDPA coated with the Lantana camara chlorophyll/9,10-diphenylanthracene).

17



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Table Legends. Table 1. Water splitting properties of organic pigments coating on ZrO2 nanoparticles layer from the ITO glass substrate with 1M KHCO3 as the electrolyte under chemiluminescence irradiation and applied negative voltages for water splitting. (LC coated with the Lantana camara chlorophyll, LCR coated with the Lantana camara chlorophyll/Rubrene,

and

LCDPA

coated

with

chlorophyll/9,10-diphenylanthracene).

18


the

Lantana

camara

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Figure 1. The mechanism of the chemiluminescence reaction by the firefly Luciferin.2

19



Figure 2. The mechanism of the chemiluminescence reaction by a glow stick.

20


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3.0 2.5

Absorption (a.u)

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


LC R DPA

2.0 1.5 1.0 0.5 0.0 300

400

500

600

700

800

Wavelength (nm) Figure 3. Absorption spectra of the pigments. LC: the Lantana camara chlorophyll, R: Rubrene and DPA: 9,10-diphenylanthracene.

21



1600

Photo Luminescence Intensity

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

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DPA R LC

1400 1200 1000 800 600 400 200 0 200

400

600

800

Wavelength (nm) Figure 4. Photoluminescence spectrum of the pigments. LC: the Lantana camara chlorophyll, R: Rubrene and DPA: 9,10-diphenylanthracene.

22


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a Photo Luminescence Intensity

2500

2000

LC LCR R

1500

1000

500

0 200

400

600

800

Wavelength (nm)

b 1600

Photo Luminescence Intensity

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


1400 1200

LCDPA LC DPA

1000 800 600 400 200 0 200

400

600

800

Wavelength (nm)

Figure 5. Photoluminescence spectrum of the pigment with the FRET phenomena. (a) Lantana

camara

chlorophyll/Rubrene

solution

and

(b)

Lantana

camara

chlorophyll/9,10-diphenylanthracene solution. (LC: the Lantana camara chlorophyll, R:

Rubrene,

DPA:

chlorophyll/Rubrene

9,10-diphenylanthracene, solution

and

LCR:

LCDPA:

chlorophyll/9,10-diphenylanthracene solution). 23


Lantana Lantana

camara camara


Figure 6. The water splitting cells with firefly-like chemiluminescence irradiation by applying negative voltages.

24


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a

Current density (A/m2)

200 LCR LCDPA

150

100

50

0 0.0

-0.2

-0.4

-0.6

-0.8

-1.0

-1.2

Potential (Voltages)

30

b

H2 generation (H2: ml/cm2.s)

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


LCR LCDPA

25 20 15 10 5 0 0

200

400

600

800 1000 1200 1400 1600 1800

Time (seconds)

Figure 7. (a) The current density of the water splitting cell by chemiluminescence irradiation and negative voltages in the electrolyte of 1 M KHCO3 water solution; (b) Hydrogen generation from the water splitting cell. (LC coated with the Lantana camara chlorophyll, LCR coated with the Lantana camara chlorophyll/Rubrene, and LCDPA coated with the Lantana camara chlorophyll/9,10-diphenylanthracene).

25



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Table 1. Water splitting properties of organic pigments coating on ZrO2 nanoparticles layer from the ITO glass substrate with 1M KHCO3 as the electrolyte under chemiluminescence irradiation and applied negative voltages for water splitting. (LC coated with the Lantana camara chlorophyll, LCR coated with the Lantana camara chlorophyll/Rubrene,

and

LCDPA

coated

with

the

Lantana

camara

chlorophyll/9,10-diphenylanthracene). J at 1.23V (A/m2)

Jop (A/m2)

1.23 - Eop (V)

η(%)

LCR

123.00

56.06

0.61

7.58%±0.5%

LCDPA

182.00

88.103

0.65

12.77%±0.6%

26


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Supporting Information Available: XRD pattern of the ZrO2 nanoparticles; morphologies of ZrO2 nanoparticles and cross section of ZrO2 nanoparticles films on ITO glass; The cyclic voltammetry curve (vs. Ag/Ag+) of the organic pigments; the energy levels (vs. vacuum energy level) of ZrO2, Lantana camara chlorophyll, Rubrene and 9,10 diphenylanthracene; the current density of chemiluminescence irradiation and dark field in the electrolyte (1 M KHCO3 water solution) of the ZrO2 nanoparticles films coated with Lantana camara chlorophyll/Rubrene and ZrO2 nanoparticles films coated with Lantana camara chlorophyll/9,10 diphenylanthracene; the volume of hydrogen generation by the water splitting cells with chemiluminescence irradiation.

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