Noncovalent Intermolecular Interactions in Organic Electronic Materials: Implications for the Molecular Packing vs Electronic Properties of Acenes

Sutton, Christopher; Risko, Chad; Brédas, Jean‐Luc

doi:10.1021/acs.chemmater.5b03266

Cited by 240 publications

(207 citation statements)

References 207 publications

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“…Overall, the present study explores the new approacht owards controlling the optical behaviour of functional dyes in the solid state, throughm anipulation of the structure of saturated rings rather than the nature of aliphatic chains. [33] Experimental Section…”

Section: Resultsmentioning

confidence: 99%

How a Small Structural Difference Can Turn Optical Properties of π‐Extended Coumarins Upside Down: The Role of Non‐Innocent Saturated Rings

Ventura

Poronik

Deperasińska

et al. 2016

Chemistry A European J

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The fluorescence properties of two new families of heterocycles possessing either a seven- or five-membered ring attached at the core molecule are entirely different in solution and in the solid state. Crystallization has the effect of inhibiting non-radiative excited-state deactivation pathways, operative in solution for the seven-membered ring compounds, thus leading to significant fluorescence efficiency in the solid state, with quantum yields ranging from 0.10 to 0.36. Conversely, the five-membered ring derivatives, which display notable emission properties in solution, are almost non-emissive in the crystalline state, characterized by a long-range π-stacked arrangement. When embedded in polymeric films, both series show fluorescence features similar to the solution case, with remarkable fluorescence quantum yields ranging from 0.09 to 0.41. According to quantum chemical calculations, 3H-chromeno[3,4-c]pyridine-4,5-diones show the specific mechanism of fluorescence quenching. The derivatives bearing the seven-membered ring undergo, in solution, a significant structural deformation in the excited state, resulting in a large decrease of the energy gap between S and S and hence to a substantial contribution of the internal conversion in the relaxation process. The fluorescence quenching of the five-membered ring derivatives is in turn related to the intermolecular interaction between adjacent molecules prevailing to a greater extent in the crystal lattice.

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Section: Resultsmentioning

confidence: 99%

How a Small Structural Difference Can Turn Optical Properties of π‐Extended Coumarins Upside Down: The Role of Non‐Innocent Saturated Rings

Ventura

Poronik

Deperasińska

et al. 2016

Chemistry A European J

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“…[67,68] For example, fluorophobic interactions from fluoroalkyl chains often induce unique self-organized architectures and to facilitate charge transport properties. [67,68] For example, fluorophobic interactions from fluoroalkyl chains often induce unique self-organized architectures and to facilitate charge transport properties.…”

Section: Reviewmentioning

confidence: 99%

Effective Use of Electrically Insulating Units in Organic Semiconductor Thin Films for High‐Performance Organic Transistors

Kang

Qiu

et al. 2016

Adv Elect Materials

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The electrical properties of organic semiconductors (OSCs), whether they are conjugated small molecules or polymers, can be tailored by incorporating electrically insulating units (EIUs), which are organic moieties consisting of nonconjugated units. EIUs can be introduced to a thin film by synthetically connecting them to the otherwise conjugated OSC molecules or by blending them in as separate EIU molecules with the OSCs during the thin‐film fabrication process. The engineered EIUs are capable of imparting various additional functions to the OSC thin film and improving their electrical properties. In this review article, a comprehensive overview of various effects of EIUs on OSC thin films and their consequent electrical performance when used as active layers in organic field‐effect transistors (OFETs) is provided. A broad range of studies of the synthetic approaches of incorporating EIUs, such as those using side chains, block copolymers, and conjugation‐break spacers, and of the blending approaches with organic insulators is discussed. Finally, a brief summary and perspectives for future research in this field are presented.

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“…[22,[34][35][36][37][38][39][40][41][42][43][44][45][46]). Specifically, Ambrosch-Draxl et al [22] have suggested that a combination of dispersion-inclusive DFT methods, which they found to predict lattice parameters in agreement with experiments for acene crystals, followed by MBPT calculations can be used to explore quantitative differences in optical properties of pentacene polymorphs.…”

Section: Introductionmentioning

confidence: 99%

Structural and excited-state properties of oligoacene crystals from first principles

et al. 2016

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Molecular crystals are a prototypical class of van der Waals (vdW) bound organic materials with excitedstate properties relevant for optoelectronics applications. Predicting the structure and excited-state properties of molecular crystals presents a challenge for electronic structure theory, as standard approximations to density functional theory (DFT) do not capture long-range vdW dispersion interactions and do not yield excited-state properties. In this work, we use a combination of DFT including vdW forces, using both nonlocal correlation functionals and pairwise correction methods, together with many-body perturbation theory (MBPT) to study the geometry and excited states, respectively, of the entire series of oligoacene crystals, from benzene to hexacene. We find that vdW methods can predict lattice constants within 1% of the experimental measurements, on par with the previously reported accuracy of pairwise approximations for the same systems. We further find that excitation energies are sensitive to geometry, but if optimized geometries are used MBPT can yield excited-state properties within a few tenths of an eV from experiment. We elucidate trends in MBPT-computed charged and neutral excitation energies across the acene series and discuss the role of common approximations used in MBPT.

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Noncovalent Intermolecular Interactions in Organic Electronic Materials: Implications for the Molecular Packing vs Electronic Properties of Acenes

Cited by 240 publications

References 207 publications

How a Small Structural Difference Can Turn Optical Properties of π‐Extended Coumarins Upside Down: The Role of Non‐Innocent Saturated Rings

How a Small Structural Difference Can Turn Optical Properties of π‐Extended Coumarins Upside Down: The Role of Non‐Innocent Saturated Rings

Effective Use of Electrically Insulating Units in Organic Semiconductor Thin Films for High‐Performance Organic Transistors

Structural and excited-state properties of oligoacene crystals from first principles

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