Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions

Jackson, Nicholas E.; Savoie, Brett M.; Kohlstedt, Kevin L.; Cruz, Mónica Olvera de la; Schatz, George C.; Chen, Lin X.; Ratner, Mark A.

doi:10.1021/ja403667s

Cited by 413 publications

(458 citation statements)

References 66 publications

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“…Indepth quantum chemical calculations highlight the hydrogen-fluorine interactions as the main reason to lock the conformation of the polymer backbone into a more planar state [62]. Other reports claim that the S … F and F … F interactions may influence the planarization [27,63,64].…”

Section: Influence Of Fluorination On the Frontier Molecular Orbitalsmentioning

confidence: 99%

Impact of Backbone Fluorination on π-Conjugated Polymers in Organic Photovoltaic Devices: A Review

et al. 2016

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Solution-processed bulk heterojunction solar cells have experienced a remarkable acceleration in performances in the last two decades, reaching power conversion efficiencies above 10%. This impressive progress is the outcome of a simultaneous development of more advanced device architectures and of optimized semiconducting polymers. Several chemical approaches have been developed to fine-tune the optoelectronics and structural polymer parameters required to reach high efficiencies. Fluorination of the conjugated polymer backbone has appeared recently to be an especially promising approach for the development of efficient semiconducting polymers. As a matter of fact, most currently best-performing semiconducting polymers are using fluorine atoms in their conjugated backbone. In this review, we attempt to give an up-to-date overview of the latest results achieved on fluorinated polymers for solar cells and to highlight general polymer properties' evolution trends related to the fluorination of their conjugated backbone.

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Section: Influence Of Fluorination On the Frontier Molecular Orbitalsmentioning

confidence: 99%

Impact of Backbone Fluorination on π-Conjugated Polymers in Organic Photovoltaic Devices: A Review

et al. 2016

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“…As a result, they capably identify the spatial extent and the underlying nature of interactions present in molecular systems and complexes. The relevance of NCI for studying large systems has been demonstrated on DNA, proteins, as well as nanotubes, 205,206 polymers, 207 and crystals under high pressure. 208 Moreover, this tool has also been used to explore reactivity, 114,184,209,210 dynamics, 191 and solvation 211 effects.…”

Section: Applicability and Usefulness Of Visualization Toolsmentioning

confidence: 99%

Perspective: Found in translation: Quantum chemical tools for grasping non-covalent interactions

Pastorczak¹,

Corminbœuf²

2017

The Journal of Chemical Physics

110

102

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Today's quantum chemistry methods are extremely powerful but rely upon complex quantities such as the massively multidimensional wavefunction or even the simpler electron density. Consequently, chemical insight and a chemist's intuition are often lost in this complexity leaving the results obtained difficult to rationalize. To handle this overabundance of information, computational chemists have developed tools and methodologies that assist in composing a more intuitive picture that permits better understanding of the intricacies of chemical behavior. In particular, the fundamental comprehension of phenomena governed by non-covalent interactions is not easily achieved in terms of either the total wavefunction or the total electron density, but can be accomplished using more informative quantities. This perspective provides an overview of these tools and methods that have been specifically developed or used to analyze, identify, quantify, and visualize non-covalent interactions. These include the quantitative energy decomposition analysis schemes and the more qualitative class of approaches such as the Non-covalent Interaction index, the Density Overlap Region Indicator, or quantum theory of atoms in molecules. Aside from the enhanced knowledge gained from these schemes, their strengths, limitations, as well as a roadmap for expanding their capabilities are emphasized. ©2017Author(s

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“…PBDTTPD is predicted by models to be almost completely planar, 61 possibly aided by intermolecular interactions between the oxygen on the TPD unit and a hydrogen on the BDT unit. 62 To investigate the effect of backbone twisting on photo-stability, we compared the photobleaching rates of PBDTTPD and its furan derivative, PBDFTPD (Figure 4). Films of the two polymers have similar densities of 1.16 and 1.12 g cm -3 .…”

Section: Bond Twisting and Photobleach Ratementioning

confidence: 99%

Molecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials

et al. 2015

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For long-term performance chemically robust materials are desired for organic solar cells (OSCs). Illuminating neat films of OSC materials in air and tracking the rate of absorption loss, or photobleaching, can quickly screen a material's photo-chemical stability. In this report, we photobleach neat films of OSC materials including polymers, solution-processed oligomers, solution-processed small molecules, and vacuum-deposited small molecules. Across the materials we test, we observe photobleaching rates that span seven orders of magnitude. Furthermore, we find that the film morphology of any particular material impacts the observed photobleaching rate, and that amorphous films photobleach faster than crystalline ones. In an extreme case, films of amorphous rubrene photobleach at a rate 2500 times faster than polycrystalline films. When we compare density to photobleaching rate, we find that stability increases with density. We also investigate the relationship between backbone planarity and chemical reactivity. The polymer PBDTTPD is more photostable than its more twisted and less ordered furan derivitative, PBDFTPD. Finally, we relate our work to what is known about the chemical stability of structural polymers, organic pigments, and organic light emitting diode materials. For the highest chemical stability, planar materials that form dense, crystalline film morphologies should be designed for OSCs.

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Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions

Cited by 413 publications

References 66 publications

Impact of Backbone Fluorination on π-Conjugated Polymers in Organic Photovoltaic Devices: A Review

Impact of Backbone Fluorination on π-Conjugated Polymers in Organic Photovoltaic Devices: A Review

Perspective: Found in translation: Quantum chemical tools for grasping non-covalent interactions

Molecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials

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