Chapter 5 Synthesis of Metal-Free Organic Dyes Containing
5.3.4 Photovoltaic properties of DSSCs
Figure 5.6 displays incident photon-to-current conversion efficiency (IPCE) and photocurrent–voltage (I–V) curves of DSSCs based on the dyes Cpd11, Cpd16, Cpd22, and N719. From Figure 5.6b, we characterized the photovoltaic parameters of
the DSSCs (Table 5.3), namely their open-circuit photovoltages (VOC), short-circuit photocurrent densities (JSC), fill factors (FFs), and solar-to-electrical energy conversion efficiencies (). The power conversion efficiencies (PCEs, i.e., η) followed the trend Cpd16 (η = 3.72) > Cpd22 (η = 2.82) > Cpd11 (η = 2.69). The highest PCE was that of the DSSC incorporating Cpd16, mainly because it had the highest short current density (Jsc = 9.98 mA cm–2), which reveals more electrons were transferred from the excited state of the dye and injected into the conduction band of TiO2; the DSSCs incorporating the three dyes each had similar values of Voc and FF.
The IPCE spectrum of Cpd16 (Figur 5.6a) featured the broadest response in the range 300–750 nm with a maximum IPCE value of 64%; this behavior is consistent with its DSSC having the highest PCE (η = 3.72; with VOC = 0.58 V; JSC = 9.98 mA cm–2; and FF = 0.65). Thus, the highest PCE (η = 3.72) for the device incorporating Cpd16 resulted from its high short current intensity (Jsc = 9.98 mA cm–2) and broadest and most-intense IPCE spectrum (toward the longer wavelength region), both of which presumably resulted from the longer conjugated structure induced by this dye’s
additional bithiophene linker. The different PCE values of Cpd11, Cpd16, and Cpd22 may be attributed to the following reasons; (i) Cpd16 and Cpd22 were bridged through a donor bithiophene linkage and an acceptor bithiazole linkage, respectively, in contrast to Cpd11; (ii) The steric effect induced by the lateral alkyl chains of the bithiazole unit might affect the conjugation of Cpd22; (iii) As noticed in Fig. 4, the greater packing nature of Cpd16 enhanced the electron injection to TiO2 and also enhanced JSC to obtain a higher PCE value.
Table 5.3 Cell performance of Cpd11, Cpd16, Cpd22, and N719-sensitized solar cells
DSSC Voc (V) Jsc (mA cm–2) FF (%) η (%)
Cpd11 0.57 –6.85 0.70 2.69
Cpd16 0.58 –9.98 0.65 3.72
Cpd22 0.60 –6.77 0.70 2.82
N719 0.70 –15.41 0.65 7.04
a Measured under AM 1.5 irradiation, 100 mW cm–2.
(a)
(b)
Figure 5.6 (a) IPCE plots of DSSCs fabricated using dyes Cpd11, Cpd16, Cpd22, and N719. (b) I-V curves of DSSCs based on dyes Cpd11, Cpd16, Cpd22, and N719.
5.4 Conclusions
We have synthesized three new metal-free organic dyes (Cpd11, Cpd16, and Cpd22), each featuring a tris(dodecyloxy)phenyl moiety (a common unit in liquid crystalline structures) as an electron donor, a cyanoacrylic acid moiety as an electron acceptor/anchoring group, and a DTT-based spacer to bridge the donor and acceptor moieties. To extend the length of conjugation, we appended a bithiophene or bithiazole moiety to the DTT unit to enhance the capacity for charge transfer and increase the range of absorption. The dye Cpd16 exhibited mesomorphic properties, resulting from the appropriate ratio of the lengths of its flexible chain to its rigid core;
molecular modeling of Cpd16, and its d-spacing value determined using XRD, verified the existence of a tilt angle in the SmC phase. In addition, among the tested dyes, the DSSC exhibiting the best performance was that incorporating Cpd16, presumably because of its superior packing as a result of its mesomorphic properties.
This DSSC exhibited a maximum PCE of 3.72% (Voc = 0.58 V; Jsc = 9.98 mA cm–2; FF = 0.65) under simulated AM 1.5 irradiation (100 mW cm–2).
Chapter 6
Conclusion
First, the concept of supermolecular interactions, such as H-bonds formed between conjugated polymers (PCA and PCB) and surface-modified nanoparticles ZnO (ZnOpy), has been introduced by the syntheses of ZnOpy nanoparticles and two fused dithienothiophene/carbazole-based polymers. The band gaps and the HOMO/LUMO energy levels of these resulting copolymers can be finely tuned as demonstrated by the investigation of optical absorption properties and electrochemical studies. The pyridyl surfactants of ZnOpy nanoparticles (as electron acceptors to partially replace expensive electron acceptor PCBM) not only induce supramolecular interactions with benzoic acid pendants of polymer PCB via H-bonds, but also enhance the homogeneous dispersions of ZnOpy nanoparticles in polymer PCB.
Thus, the PSC device containing ternary components of polymer PCB blended with ZnOpy and PCBM acceptors (PCB:ZnOpy:PCBM=1:0.05:1) had the power
conversion efficiency of up to 0.55%, which gave the best performance with the values of Isc=2.11mA/cm2, FF=29.4%, and Voc=0.88 V.Second, We have successfully synthesized three dithienothiophene/ carbazole-based conjugated polymers (PCC, PCA and PCB) by Suzuki coupling reaction. Interestingly, PCC, PCA and PCB
exhibited reversible electrochromism during the oxidation processes of cyclic
voltammogram studies. Among PCC, PCA and PCB, polymer PCB (with H-bonds) revealed the best electrochromic property with the most noticeable color change. In powder X-ray diffraction (XRD) measurements, these polymers exhibited obvious diffraction features indicating distinct bilayered packings between polymer backbones and similar p-p stacking between layers in the solid state. Compared with the XRD data of PCA (without H-bands), H-bonds of PCB induced a higher crystallinity in the small angle region (corresponding to a higher ordered bilayered packings between polymer backbones), but with a similar crystallinity in the wide angle region indicating a comparable π–π stacking distance between layers. The potential applications of PCC, PCA and PCB in bulk heterojunction photovoltaic solar cells (PSCs) were further investigated, where the PSC device containing PCB blended with PCBM (by a weight ratio of 1:1) had the optimum power conversion efficiency (PCE) up to 0.61% (with Jsc = 2.26 mA/cm2, FF = 29.8%, and Voc = 0.90 V). Due to the H-bonded effects, polymer PCB possessed higher thermal decomposition temperature (Td), glass transition temperature (Tg), RMS smoothness, open circuit voltage (Voc), and PCE value than PCA. These polymers demonstrate a novel family of conjugated polymers along the path toward achieving the electrochromic and PSC applications.
Third, We synthesized a series of metallo-polymers (P1-P4) with aryl-imidazo-phenanthrolines (AIP) units (incorporated with phenyl and fused
dithienothiophene groups in different donor spacers) to study for their electrochemical and electrochromic properties. In order to investigate the energy transfers between metallo-polymers (P1-P4) and nanoparticle ZnOpy, novel supramolecular nanocomposites P3-P4/ZnOpy were constructed by complexation of proton donor (H-donor) metallo-polymers P3-P4, consisting of carboxylic acid groups, with proton accepter (H-accepter) ZnOpy. They were compared with nanocomposites P1-P2/ZnOpy containing metallo-polymers P1-P2 without carboxylic acid groups to
have no H-bonded interactions with nanoparticle ZnOpy. In contrast to amorphous metallo-polymers P3-P4 from XRD measurements, supramolecular nanocomposites P3-P4/ZnOpy exhibited obvious diffraction features (originated from metallo-polymers P3-P4) indicating the increased crystallinities of P3-P4 upon addition of ZnOpy, due to the supramolecular (H-bonded) interactions. TEM morphologies also proved that the supramolecular (H-bonded) interactions between ZnOpy and polymers P3-P4 induce nanoparticles to be homogeneously dispersed in
nanocomposites P3-P4/ZnOpy.
Finally, We have synthesized three new metal-free organic dyes (Cpd11, Cpd16, and Cpd22), each featuring a tris(dodecyloxy)phenyl moiety (a common unit in liquid
crystalline structures) as an electron donor, a cyanoacrylic acidmoiety as an electron acceptor/anchoring group, and a DTT-based spacer to bridge the donor and acceptor
moieties. To extend the length of conjugation, we appended a bithiophene or bithiazole moiety to the DTT unit to enhance the capacity for charge transfer and increase the range of absorption. The dye Cpd16 exhibited mesomorphic properties, resulting from the appropriate ratio of the lengths of its flexible chain to its rigid core;
molecular modeling of Cpd16, and its d-spacing value determined using XRD, verified the existence of a tilt angle in the SmC phase. In addition, among the tested dyes, the DSSC exhibiting the best performance was that incorporating Cpd16, presumably because of its superior packing as a result of its mesomorphic properties.
This DSSC exhibited a maximum PCE of 3.72% (Voc = 0.58 V; Jsc = 9.98 mA cm–2; FF = 0.65) under simulated AM 1.5 irradiation (100 mW cm–2).
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Publication
1. Hsiao-Ping Fang, I-Hung Chiang, Chih-Wei Chu, Chang-Chung Yang, Hong-Cheu Lin* “Applications of novel dithienothiophene- and 2,7-carbazole-based conjugated polymers with
surface-modified ZnO nanoparticles for organic photovoltaic cells”, Thin Solid Films 2011, 519, 5212-5218.
2. Hsiao-Ping Fang, Jia-Wei Lin, I-Hung Chiang, Chih-Wei Chu, Kung-Hwa Wei, Hong-Cheu Lin. “ Synthesis of Novel
Dithienothiophene- and 2,7-Carbazole-Based Conjugated Polymers and H-Bonded Effects on Electrochromic and
Photovoltaic Properties” J. of Polymer Sci. Part A: Polymer Chem.
2012, 50, 5011-5022.
3. Hsiao-Ping Fang,Yen-Hsing Wu, and Hong-Cheu Lin “ Synthesis and study of novel supramolecular nanocomposites containing aryl-imidazo-phenanthroline-based metallo-polymers (H-donors) and surface-modified ZnO nanoparticles (H-acceptors) ”
Tetrahedron 2013, 69, 293-301.
4. Muthaiah Shellaiah, Hsiao-Ping Fang, Ying-Ling Lin,Ying-Chan Hsu, Jiann-T’suen Lin, and Hong-Cheu Lin “Synthesis of Metal-Free Organic Dyes Containing Tris(dodecyloxy)phenyl and
Dithienothiophenyl Units and a Study of Their Mesomorphic and Photovoltaic Properties” Tetrahedron 2012, in press.