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NASA NTRS2002

Novel High Efficient Organic Photovoltaic Materials: Appendix for Summary of Research

There are many different kinds of conjugated polymers that may be useful in photovoltaic devices. So far, the most popular and successful conjugated polymers used in photovoltaic devices include poly(1,4-)phenylenevinylenes (PPV), C60 and their derivatives. The discovery of electro-luminescence in PPV has stimulated a great deal of interest in developing "plastic" solid-state semiconductor devices. The overall synthetic methodology for the preparation of PPV can be divided into three main categories: (1) side chain derivatization, (2) precursor approach, and (3) in-situ polymerization. In this project, the first method was adopted. As discussed in project proposal and literatures, the overall efficiency of photovoltaic devices containing conjugated polymers is determined by the materials ability to generate excitons from incoming radiation, and then to separate the charges at donor/acceptor interfaces, and then to transport charges to respective electrodes. Given that effective exciton diffusion range are typical less then 30 nm, unique morphological structures are needed. This need led to several research groups to the idea that interpenetrating or bi-continuous networks of donor (electron donating) and acceptor (electron withdrawing) polymers should give better results. One approach involved the use of functionalized PPV. The attachment of electron withdrawing cyano groups to a PPV forms the CN-PPV, making it a strong electron acceptor. Underivatized PPV is a generally considered a hole-transporting material. Using blends of MEH-PPV, a soluble donor PPV derivative, as a hole transporter and CN-PPV as an electron transporter, a quantum efficiencies of up to 6% was achieved.

Sun, Sam↗

NASA NTRS2008

Multifunctional Nanotube Polymer Nanocomposites for Aerospace Applications: Adhesion between SWCNT and Polymer Matrix

Multifunctional structural materials can enable a novel design space for advanced aerospace structures. A promising route to multifunctionality is the use of nanotubes possessing the desired combination of properties to enhance the characteristics of structural polymers. Recent nanotube-polymer nanocomposite studies have revealed that these materials have the potential to provide structural integrity as well as sensing and/or actuation capabilities. Judicious selection or modification of the polymer matrix to promote donor acceptor and/or dispersion interactions can improve adhesion at the interface between the nanotubes and the polymer matrix significantly. The effect of nanotube incorporation on the modulus and toughness of the polymer matrix will be presented. Very small loadings of single wall nanotubes in a polyimide matrix yield an effective sensor material that responds to strain, stress, pressure, and temperature. These materials also exhibit significant actuation in response to applied electric fields. The objective of this work is to demonstrate that physical properties of multifunctional material systems can be tailored for specific applications by controlling nanotube treatment (different types of nanotubes), concentration, and degree of alignment.

Park, Cheol↗

NASA NTRS2001

Synthesis and Characterization of SF-PPV-I

Conjugated electro-active polymers find their potential applications in developing variety inexpensive and flexible shaped electronic and photonic devices, such as photovoltaic or photo/electro light emitting devices. In many of these opto-electronic polymeric materials, certain electron rich donors and electron deficient acceptors are needed in order to fine-tune the electronic or photonic properties of the desired materials and structures. While many donor type of conjugated polymers have been widely studied and developed in the past decades, there are relatively fewer acceptor type of conjugated polymers have been developed. Key acceptor type conjugated polymers developed so far include C60 and CN-PPV, and each has its limitations. Due to the complexity and diversity of variety future electronic materials and structural needs, alternative and synthetically amenable acceptor conjugated polymers need to be developed. In this paper, we present the synthesis and characterization of a new acceptor conjugated polymer, a sulfone derivatized polyphenylenevinylene "SF-PPV".

Wang, Y.↗

NASA NTRS2010

Dispersions of Carbon nanotubes in Polymer Matrices

Dispersions of carbon nanotubes exhibiting long term stability are based on a polymer matrix having moieties therein which are capable of a donor-acceptor complexation with carbon nanotubes. The carbon nanotubes are introduced into the polymer matrix and separated therein by standard means. Nanocomposites produced from these dispersions are useful in the fabrication of structures, e.g., lightweight aerospace structures.

Wise, Kristopher Eric↗

NASA NTRS1983

Towards an organic photobattery - Photovoltaic properties of some thermal copolyamino acids

Thermal copolymers of amino acids have been examined as a novel material for photovoltaic devices. Due to the steric effects of amino acids during polymerization, these polymers are highly ordered, and pigments such as flavins and pterins are formed as part of the polymer. The controllably varied composition of the amino acids in the polymer makes it possible to get either electron-donor or electron-acceptor, or both kinds of groups in varying degrees. The constituent photosensitive element has been made either of photosensitive polymer film or spherule.

Przybylski, A. T.↗

NASA NTRS1999

Electronically conducting polymers with silver grains

The present invention provides electronically conducting polymer films formed from photosensitive formulations of pyrrole and an electron acceptor that have been selectively exposed to UV light, laser light, or electron beams. The formulations may include photoinitiators, flexibilizers, solvents and the like. These solutions can be used in applications including printed circuit boards and through-hole plating and enable direct metallization processes on non-conducting substrates. After forming the conductive polymer patterns, a printed wiring board can be formed by sensitizing the polymer with palladium and electrolytically depositing copper.

Murphy, Oliver J.↗

NASA NTRS2001

Method of forming electronically conducting polymers on conducting and nonconducting substrates

Murphy, Oliver J.↗

NASA NTRS1975

Synthesis and evaluation of polymers for use in early warning fire alarm devices

Conjugated polyacetylene polymers and one condensation polyene, all containing a high degree of conjugated unsaturation, were synthesized. These polymers were characterized by chemical analysis and by thermogravimetric analysis, as well as for their film-forming capability and gas/polymer interactions. It was found that those that had a high degree of conjugated unsaturation and had resonance - stabilizing groups were very thermally stable to 200 C, e.g., poly(dicyanoacetylene), poly(ethynylferrocene) and poly(phenylacetylene); while those with labile moieties, such as poly(p-formamidophenylacetylene), among others, suffered some degradation when heated in air. When subjected to gas/polymer interaction effects, the greatest change in electrical conductance was observed when ammonia was used as the gas and poly(p-nitrophenylacetylene) was the detector. Other polymers showed similar behavior. For example, poly(ethynylcarborane), considered to be an electron acceptor also showed a change in electrical conductance when exposed to ammonia, while poly(ethynylpyridine) and poly(ethylidenepyridazine) responded to carbon monoxide. However, for "fire gases" (gases from smoldering cotton), poly(ethynylferrocene) was the most responsive. Thus, the concept of polymers with different electronegativities forming charge-transfer complexes with different gases was found to be operable.

Byrd, N. R.↗

NASA NTRS2002

Design and Synthesis of Novel Block Copolymers for Efficient Opto-Electronic Applications

It has been predicted that nano-phase separated block copolymer systems containing electron rich donor blocks and electron deficient acceptor blocks may facilitate the charge carrier separation and migration in organic photovoltaic devices due to improved morphology in comparison to polymer blend system. This paper presents preliminary data describing the design and synthesis of a novel Donor-Bridge-Acceptor (D-B-A) block copolymer system for potential high efficient organic optoelectronic applications. Specifically, the donor block contains an electron donating alkyloxy derivatized polyphenylenevinylene (PPV), the acceptor block contains an electron withdrawing alkyl-sulfone derivatized polyphenylenevinylene (PPV), and the bridge block contains an electronically neutral non-conjugated aliphatic hydrocarbon chain. The key synthetic strategy includes the synthesis of each individual block first, then couple the blocks together. While the donor block stabilizes and facilitates the transport of the holes, the acceptor block stabilizes and facilitates the transport of the electrons, the bridge block is designed to hinder the probability of electron-hole recombination. Thus, improved charge separation and stability are expected with this system. In addition, charge migration toward electrodes may also be facilitated due to the potential nano-phase separated and highly ordered block copolymer ultra-structure.

Sun, Sam-Shajing↗

NASA NTRS2005

Improved Charge-Transfer Fluorescent Dyes

Improved charge-transfer fluorescent dyes have been developed for use as molecular probes. These dyes are based on benzofuran nuclei with attached phenyl groups substituted with, variously, electron donors, electron acceptors, or combinations of donors and acceptors. Optionally, these dyes could be incorporated as parts of polymer backbones or as pendant groups or attached to certain surfaces via self-assembly-based methods. These dyes exhibit high fluorescence quantum yields -- ranging from 0.2 to 0.98, depending upon solvents and chemical structures. The wavelengths, quantum yields, intensities, and lifetimes of the fluorescence emitted by these dyes vary with (and, hence, can be used as indicators of) the polarities of solvents in which they are dissolved: In solvents of increasing polarity, fluorescence spectra shift to longer wavelengths, fluorescence quantum yields decrease, and fluorescence lifetimes increase. The wavelengths, quantum yields, intensities, and lifetimes are also expected to be sensitive to viscosities and/or glass-transition temperatures. Some chemical species -- especially amines, amino acids, and metal ions -- quench the fluorescence of these dyes, with consequent reductions in intensities, quantum yields, and lifetimes. As a result, the dyes can be used to detect these species. Another useful characteristic of these dyes is a capability for both two-photon and one-photon absorption. Typically, these dyes absorb single photons in the ultraviolet region of the spectrum (wavelengths < 400 nm) and emit photons in the long-wavelength ultraviolet, visible, and, when dissolved in some solvents, near-infrared regions. In addition, these dyes can be excited by two-photon absorption at near-infrared wavelengths (600 to 800 nm) to produce fluorescence spectra identical to those obtained in response to excitation by single photons at half the corresponding wavelengths (300 to 400 nm). While many prior fluorescent dyes exhibit high quantum yields, solvent-polarity- dependent fluorescence behavior, susceptibility to quenching by certain chemical species, and/or two-photon fluorescence, none of them has the combination of all of these attributes. Because the present dyes do have all of these attributes, they have potential utility as molecular probes in a variety of applications. Examples include (1) monitoring curing and deterioration of polymers; (2) monitoring protein expression; (3) high-throughput screening of drugs; (4) monitoring such chemical species as glucose, amines, amino acids, and metal ions; and (5) photodynamic therapy of cancers and other diseases.

Meador, Michael↗

NASA NTRS1989

All-Optical Photochromic Spatial Light Modulators

Photochemical transfer of electrons enables fast reading and writing. New concept based on transfer of electrons between donor and acceptor molecules randomly distributed or covalently linked and dispersed in glassy-polymer host material. Transfer causes significant changes in optical-transmission characteristics of material and used to modulate transmission of reading beam of light impinging on material.

Beratan, David N.↗

NASA NTRS2003

Novel High Efficient Organic Photovoltaic Materials

Solar energy is a renewable, nonpolluting, and most abundant energy source for human exploration of a remote site or outer space. In order to generate appreciable electrical power in space or on the earth, it is necessary to collect sunlight from large areas and with high efficiency due to the low density of sunlight. Future organic or polymer (plastic) solar cells appear very attractive due to their unique features such as light weight, flexible shape, tunability of energy band-gaps via versatile molecular or supramolecular design, synthesis, processing and device fabrication schemes, and much lower cost on large scale industrial production. It has been predicted that supramolecular and nano-phase separated block copolymer systems containing electron rich donor blocks and electron deficient acceptor blocks may facilitate the charge carrier separation and migration due to improved electronic ultrastructure and morphology in comparison to polymer composite system. This presentation will describe our recent progress in the design, synthesis and characterization of a novel block copolymer system containing donor and acceptor blocks covalently attached. Specifically, the donor block contains an electron donating alkyloxy derivatized polyphenylenevinylene (RO-PPV), the acceptor block contains an electron withdrawing alkyl-sulfone derivatized polyphenylenevinylene (SF-PPV). The key synthetic strategy includes the synthesis of each individual block first, then couple the blocks together. While the donor block has a strong PL emission at around 560 nm, and acceptor block has a strong PL emission at around 520 nm, the PL emissions of final block copolymers are severely quenched. This verifies the expected electron transfer and charge separation due to interfaces of donor and acceptor nano phase separated blocks. The system therefore has potential for variety light harvesting applications, including high efficient photovoltaic applications.

Sun, Sam↗

NASA NTRS1999

In vitro activities of four xyloglucan endotransglycosylases from Arabidopsis

Xyloglucan endotransglycosylases (XETs) are encoded by a gene family in Arabidopsis thaliana. These enzymes modify a major structural component of the plant cell wall, xyloglucan, and therefore may influence plant growth and development. We have produced four Arabidopsis XETs (TCH4, Meri-5, EXGT and XTR9) using the baculovirus/insect cell system and compared their biochemical activities. TCH4, as previously demonstrated, and the other three proteins are capable of carrying out transglycosylation of xyloglucans. The K(m) for XLLGol acceptor oligosaccharide is in the range of 20-40 microM for all the XETs except XTR9, which has a Km of 5 microM and is significantly inhibited by high levels of XLLGol. All four enzymes are most active between pH 6.0 and 6.5. TCH4 and XTR9 have temperature optima of 18 degrees C, whereas Meri-5 and EXGT are most active at 28 and 37 degrees C, respectively. Although the activity levels of three of the XETs are not influenced by the presence of fucose on the xyloglucan polymer, XTR9 has a clear preference for non-fucosylated xyloglucan polymer. The four XETs show a marked preference for XLLGol over either XXFGol or XXXGol as acceptor oligosaccharide. All four XETs are glycosylated; however, only the activities of TCH4 and Meri-5 are affected by the removal of the N-glycan with PNGase F. These four enzymes most likely function solely as transglycosylases because xyloglucan endoglucanase activity was not apparent. Subtle differences in biochemical activities may influence the physiological functions of the distinct XETs in vivo.

Non-NASA Center↗

NASA NTRS2001

Novel High Efficient Organic Photovoltaic Materials

In man's mission to the outer space or a remote site, the most abundant, renewable, nonpolluting, and unlimited external energy source is light. Photovoltaic (PV) materials can convert light into electrical power. In order to generate appreciable electrical power in space or on the Earth, it is necessary to collect sunlight from large areas due to the low density of sunlight, and this would be very costly using current commercially available inorganic solar cells. Future organic or polymer based solar cells seemed very attractive due to several reasons. These include lightweight, flexible shape, ultra-fast optoelectronic response time (this also makes organic PV materials attractive for developing ultra-fast photo detectors), tunability of energy band-gaps via molecular design, versatile materials synthesis and device fabrication schemes, and much lower cost on large-scale industrial production. It has been predicted that nano-phase separated block copolymer systems containing electron rich donor blocks and electron deficient acceptor blocks will facilitate the charge separation and migration due to improved electronic ultrastructure and morphology in comparison to current polymer composite photovoltaic system. This presentation will describe our recent progress in the design, synthesis and characterization of a novel donor-bridge-acceptor block copolymer system for potential high-efficient organic optoelectronic applications. Specifically, the donor block contains an electron donating alkyloxy derivatized polyphenylenevinylene, the acceptor block contains an electron withdrawing alkyl-sulfone derivatized polyphenylenevinylene, and the bridge block contains an electronically neutral non-conjugated aliphatic hydrocarbon chain. The key synthetic strategy includes the synthesis of each individual block first, then couple the blocks together. While the donor block stabilizes the holes, the acceptor block stabilizes the electrons. The bridge block is designed to hinder the electron-hole recombination. Thus, improved charge separation is expected. In addition, charge migration will also be facilitated due to the expected nano-phase separated and highly ordered block copolymer ultrastructural. The combination of all these factors will result in significant overall enhancement of photovoltaic power conversion efficiency.

Sun, Sam↗

NASA NTRS1991

Molecules with enhanced electronic polarizabilities based on defect-like states in conjugated polymers

Highly conjugated organic polymers typically have large non-resonant electronic susceptibilities, which give the molecules unusual optical properties. To enhance these properties, defects are introduced into the polymer chain. Examples include light doping of the conjugated polymer and synthesis, conjugated polymers which incorporate either electron donating or accepting groups, and conjugated polymers which contain a photoexcitable species capable of reversibly transferring its electron to an acceptor. Such defects in the chain permit enhancement of the second hyperpolarizability by at least an order of magnitude.

Beratan, David N.↗

NASA NTRS2001

Thin-Film Organic-Based Solar Cells for Space Power

Recent advances in dye-sensitized and organic polymer solar cells have lead NASA to investigate the potential of these devices for space power generation. Dye-sensitaized solar cells were exposed to simulated low-earth orbit conditions and their performance evaluated. All cells were characterized under simulated air mass zero (AM0) illumination. Complete cells were exposed to pressures less than 1 x 10 (exp -7)torr for over a month, with no sign of sealant failure or electrolyte leakage. Cells from Solaronix SA were rapid thermal cycled under simulated low-earth orbit conditions. The cells were cycled 100 times from -80 C to 80 C, which is equivalent to 6 days in orbit. The best cell had a 4.6% loss in efficiency as a result of the thermal cycling. In a separate project, novel -Bridge-Donor-Bridge-Acceptor- (-BDBA-) type conjugated block copolymer systems have been synthesized and characterized by photoluminescence (PL). In comparison to pristine donor or acceptor, the PL emissions of final -B-D-B-A- block copolymer films were quenched over 99%. Effective and efficient photo induced electron transfer and charge separation occurs due to the interfaces of micro phase separated donor and acceptor blocks. The system is very promising for a variety high efficiency light harvesting applications. Under an SBIR contract, fullerene-doped polymer-based photovoltaic devices were fabricated and characterized. The best devices showed overall power efficiencies of approximately 0.14% under white light. Devices fabricated from 2% solids content solutions in chlorobenzene gave the best results. Presently, device lifetimes are too short to be practical for space applications.

Bailey, Sheila G.↗

NASA NTRS2002

Thin-film Organic-based Solar Cells for Space Power

Recent advances in dye-sensitized and organic polymer solar cells have lead NASA to investigate the potential of these devices for space power generation. Dye-sensitized solar cells were exposed to simulated low-earth orbit conditions and their performance evaluated. All cells were characterized under simulated air mass zero (AM0) illumination. Complete cells were exposed to pressures less than 1 x 10(exp -7) torr for over a month, with no sign of sealant failure or electrolyte leakage. Cells from Solaronix SA were rapid thermal cycled under simulated low-earth orbit conditions. The cells were cycled 100 times from -80 C to 80 C, which is equivalent to 6 days in orbit. The best cell had a 4.6 percent loss in efficiency as a result of the thermal cycling. In a separate project, novel -Bridge-Donor-Bridge- Acceptor- (-BDBA-) type conjugated block copolymer systems have been synthesized and characterized by photoluminescence (PL). In comparison to pristine donor or acceptor, the PL emissions of final -B-D-B-A- block copolymer films were quenched over 99 percent. Effective and efficient photo induced electron transfer and charge separation occurs due to the interfaces of micro phase separated donor and acceptor blocks. The system is very promising for a variety high efficiency light harvesting applications. Under an SBIR contract, fullerene-doped polymer-based photovoltaic devices were fabricated and characterized. The best devices showed overall power efficiencies of approx. 0.14 percent under white light. Devices fabricated from 2 percent solids content solutions in chlorobenzene gave the best results. Presently, device lifetimes are too short to be practical for space applications.

Bailey, Sheila G.↗

NASA NTRS1988

Second and third order nonlinear optical properties of conjugated molecules and polymers

Second- and third-order nonlinear optical properties of some newly synthesized organic molecules and polymers are reported. Powder second-harmonic-generation efficiencies of up to 200 times urea have been realized for asymmetric donor-acceptor acetylenes. Third harmonic generation chi(3)s have been determined for a series of small conjugated molecules in solution. THG chi(3)s have also been determined for a series of soluble conjugated copolymers prepared using ring-opening metathesis polymerization. The results are discussed in terms of relevant molecular and/or macroscopic structural features of these conjugated organic materials.

Perry, Joseph W.↗