Precursor polymorph determines the organic semiconductor structure formed upon annealing

Pandolfi, Lorenzo; Giunchi, Andrea; Rivalta, Arianna; D’Agostino, Simone; Valle, Raffaele Guido Della; Mas‐Torrent, Marta; Lanzi, Massimiliano; Venuti, Elisabetta; Salzillo, Tommaso

doi:10.1039/d1tc01313k

Cited by 7 publications

(13 citation statements)

References 45 publications

(66 reference statements)

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“…It is instead surprising that the mobility of γ-QA is comparable to that of sublimed β-QA, considering that the transfer integrals are much smaller. Of course, one must keep in mind that we are comparing operational mobilities, strongly dependent on the device fabrication. ,, But we have also seen that in the case of β-QA, apparently well-grown crystal faces will likely present directional disorder and that there are the two abovementioned “killer modes” along the stack direction, two facts that may easily hamper transport in a strongly anisotropic (quasi 1D) semiconductor. On the other hand, mobility in γ-QA might be favored by the fact that the naturally grown bc crystal face of the device is the one where the transport may more easily occur, also considering the virtually null lattice distortion energy along the c direction (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…This selectively triggers the formation on silicon oxide of the semiconductor α I metastable structure, whereas upon heating the most common t Boc-QA form I, β-QA is obtained. 16 This finding exemplifies how exerting control over the crystalline phase of a given compound may require knowledge of the chemical and thermal history of the sample. The crystal-to-crystal transformation that leads from t Boc-QA form II to α I -QA is not limited to the thin film phases of the two compounds.…”

Section: γ-Qa Polymorphmentioning

confidence: 88%

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Lattice Dynamics of Quinacridone Polymorphs: A Combined Raman and Computational Approach

Giunchi,

Pandolfi,

Della Valle

et al. 2023

Crystal Growth & Design

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Polarized low-frequency Raman microscopy and a posteriori dispersion-corrected density functional simulations are combined to investigate the lattice vibrations of the α I , β, and γ polymorphs of the model organic semiconductor quinacridone, which are known to display different optical and electronic properties. The comparison between experiments and calculations allows for unambiguous mode assignment and identification of the scattering crystal faces. Conversely, the agreement between simulations and experiments validates the adopted computational methods, which correctly describe the intermolecular interaction of the molecular material. The acquired knowledge of quinacridone lattice dynamics is used to describe the α I to β thermal transition and, most consequentially, to reliably characterize the electron−lattice phonon coupling strength of the three polymorphs, obtaining hints about the electrical transport mechanism of the material.

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Section: Resultsmentioning

confidence: 99%

Section: γ-Qa Polymorphmentioning

confidence: 88%

Lattice Dynamics of Quinacridone Polymorphs: A Combined Raman and Computational Approach

Giunchi,

Pandolfi,

Della Valle

et al. 2023

Crystal Growth & Design

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“…5a). 18,[33][34][35][36][37][38] This technique consists in placing a solution of the organic material between a bar and a heated substrate forming a confined meniscus and, immediately afterwards, displacing the substrate at a constant speed. It has also been shown that the use of polymer blends facilitates the processing of the films, the crystallisation of the semiconductor and the device stability.…”

Section: Resultsmentioning

confidence: 99%

Charge transfer complexes of a benzothienobenzothiophene derivative and their implementation as active layer in solution-processed thin film organic field-effect transistors

et al. 2022

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“…The polymorphism of a number of natural dyes, functional to the manufacture of OFETs, has been studied in the last years and very recently summarized. [27,94] Most of these structures show peculiar properties once deposited on suitable technological substrates, [95][96][97] resulting in the stabilization of the metastable forms on the surface. The example shortly reported here is thioindigo (2-(3-Oxo-1-benzothiophen-2(3H)-ylidene)-1-benzothiophen-3(2H)-one), that displays two polymorphs, α and β, both monoclinic with two molecules per unit cell.…”

Section: Thioindigo (2-(3-oxo-1-benzothiophen-2(3h)-ylidene)-1benzoth...mentioning

confidence: 99%

A New Approach to Polymorphism in Molecular Crystals: Substrate‐Mediated Structures Revealed by Lattice Phonon Dynamics

Salzillo

Brillante

2022

Adv Materials Inter

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The experimental search for polymorph screening is often assisted by computational studies on crystal structure predictions. [8] Lastly, a subtle perspective of Bernstein cleared up a final revision of the terminology and of the nomenclature of multiple crystal forms. [9] In more recent years a new approach to polymorphism has taken momentum in the search of new crystal structures of organic materials, the so-called thin film structures or substrate-induced polymorphs (SIP), meaning a phase grown in the vicinity of a substrate with a distinct structure from those of the bulk. [10] An earlier discussion on the subject was held in a dedicated workshop about fifteen years ago. [11] At that time the discussion was mostly focused on organic semiconductors such as pentacene and perylene diimide derivatives. Since the majority of the thin film structures showed crystal parameters not very dissimilar from those of the corresponding parent bulk forms, these structures were indicated as "distortedbulk," where the term "distorted" was ascribed to the perturbation of the substrate on the molecular layers. Approximately ten years later, [12] a new grammar on substrate-induced structures was established. The growth at the interface of a variety of different substrates led to the definition of the general class of surface-mediated structures, portraying more detailed definitions such as "surface-induced" and "surface-selected" polymorphs, with the former indicating a bulk-distorted form and the latter being a new genuine structure with no association to any crystal phase of the bulk. This is the nomenclature that we shall initially follow in the present survey, with some new hints on additional cases that will be encountered, such as substratestabilized polymorphs, as detailed further on.Certainly, the starting point of surface-mediated polymorphs cannot be separated by the exhaustive review on SIP as discussed in Jones et al. [10] In that paper, examples of sixteen molecules were given, for which thin film polymorphs had been observed on solid substrates, showing new structures with respect to the previously known single crystals polymorphs. The impact of polymorphism on the material properties was mostly addressed on organic electronics, because every structure has its own mobility with relevant consequences on the efficiency of the device. Besides, it is wellThe issue of polymorphism in molecular crystals is discussed, taking into account the substrate-mediated structures, that is, structures grown at the interface of different substrates. Bulk and thin films of a compound both share the potentiality to display different crystal forms. However, unlike bulk polymorphs, whose structures are determined by their different molecular packing, thin film structures depend very much on the molecular organization of the organic layers on the substrate, which may, or may not, lead to an ordered structure, depending on the nature of the interface and on the growth conditions. Based on large part in some of the authors' recent works, the...

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Precursor polymorph determines the organic semiconductor structure formed upon annealing

Abstract: tBoc-quinacridone films obtained by the spin coating and bar‐assisted meniscus shearing methods were subjected to thermal deprotection to recover the organic semiconductor quinacridone in its crystalline form. We found that...

Cited by 7 publications

References 45 publications

Lattice Dynamics of Quinacridone Polymorphs: A Combined Raman and Computational Approach

Lattice Dynamics of Quinacridone Polymorphs: A Combined Raman and Computational Approach

Charge transfer complexes of a benzothienobenzothiophene derivative and their implementation as active layer in solution-processed thin film organic field-effect transistors

A New Approach to Polymorphism in Molecular Crystals: Substrate‐Mediated Structures Revealed by Lattice Phonon Dynamics

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