Exploring the 3-(phenylethynyl)-9H-carbazole unit in the search of deep-blue emitting fluorophores

Bujaldón, Roger; Peřinka, Nikola; Reig, Marta; Cuadrado, Alba; Fabregat, Clara Pérez; Font-Bardı́a, Mercè; Martínez‐Ferrero, Eugenia; Velasco, Dolores

doi:10.1016/j.optmat.2020.110696

Cited by 3 publications

(3 citation statements)

References 48 publications

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“…Keeping in mind the importance of the intermolecular disposition and arrangement of the organic semiconductor, herein, we considered the synthesis of derivatives featuring flexible alkyl chains with different lengths and substitution patternings. The diindolo[3,2- b :2′,3′- h ]carbazole structure possesses three nitrogens that can be alkylated, offering the opportunity to improve the solubility and adjust the intermolecular arrangement without modifying the main core properties. ,− Of these, one corresponds to the central carbazole unit while the other two are situated in the peripheral indole extensions. Consequently, the system permits a homogeneous alkylation patterning, with all three alkyl chains displaying the same length, or a heterogeneous one by varying only the length of the peripheral N -alkyl chains.…”

Section: Introductionmentioning

confidence: 99%

Insight into the Diindolo[3,2-b:2′,3′-h]carbazole Core as an Air-Stable Semiconductor for OTFTs

Bujaldón

Vilche

Puigdollers

et al. 2023

ACS Appl. Electron. Mater.

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Encouraged by the outstanding performance of pentacene, the perspective over enhanced organic semiconductors has been focused on studying analogous ladder-type materials. In this context, the case of the diindolo[3,2-b:2′,3′-h]carbazole core is a promising example of a semiconductor with improved stability. Herein, we report the synthesis of five diindolo[3,2-b:2′,3′-h]carbazole derivatives displaying different alkylation patterning, as well as their integration in organic thin-film transistors. The elucidation of the single-crystal structures of three of the derivatives, accomplished by means of powder X-ray diffraction (PXRD), provided further insight into the intermolecular disposition of this core. As a result, the relationship between the structural design and the performance of the final devices could be analyzed. Globally, a scope of mobility values from 10–6 to 10–3 cm2 V–1 s–1 was achieved by just fine-tuning the length of the alkyl chains and the type of passivation layer applied onto the SiO2 surface. Remarkably, all the fabricated devices excel in terms of temporal and air stability with a shelf lifetime up to years, a coveted feature in organic electronics that confirms the potential of this core.

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Section: Introductionmentioning

confidence: 99%

Insight into the Diindolo[3,2-b:2′,3′-h]carbazole Core as an Air-Stable Semiconductor for OTFTs

Bujaldón

Vilche

Puigdollers

et al. 2023

ACS Appl. Electron. Mater.

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“…Carbazole is a recurrent and highly versatile scaffold within chemistry, biomedicine, and materials science because of its attractive luminescent and semiconductor properties, which can be fine-tuned through not only the subtle and rational modification of its molecular structure but also imparting control over the interactions established with the environment at the supramolecular level. − …”

Section: Introductionmentioning

confidence: 99%

Programming Positive Mechanofluorescence in Liquid Crystalline Elastomers

Güixens-Gallardo,

Brea,

Manrique

et al. 2023

ACS Appl. Polym. Mater.

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Liquid single crystal elastomers (LSCEs) containing organic fluorophores within their polymeric network are attractive materials to detect forces with simple spectroscopic measurements. Hitherto, all mechanoluminescent LSCEs decrease their emission intensity upon mechanical stimulation; that is, they display negative mechanofluorescence. Such behavior is governed by the mechanically induced approximation of the quenching mesogenic units and the fluorophores. In this work, we propose the integration of fluorescent molecular rotors (FMRs), whose luminescence is not quenched by the mesogens, in LSCEs as a valuable strategy to conceive elastomeric materials programmed with exactly the opposite behavior, i.e., their fluorescence increases upon deformation (positive mechanofluorescence). Specifically, carbazole-indolenine dyes are interesting candidates for this purpose since their luminescence depends mainly on the degree of intramolecular rotation allowed by the local environment. On this basis, the uniaxial deformation of an LSCE, along its anisotropic direction, incorporating such FMRs will place the fluorophores in a more restricted medium, leading to the desired enhanced emission at the macroscale.

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“…Carbazole as a synthetic building block also represents an important source of organic molecules with assorted applications within the optoelectronic field. In fact, it does not only stand as a promising scaffold for new organic semiconductors, but also displays outstanding photophysical properties [9,[20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Towards the Bisbenzothienocarbazole Core: A Route of Sulfurated Carbazole Derivatives with Assorted Optoelectronic Properties and Applications

2021

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Ladder-type molecules, which possess an extended aromatic backbone, are particularly sought within the optoelectronic field. In view of the potential of the 14H-bis[1]benzothieno[3,2-b:2’,3’-h]carbazole core as a p-type semiconductor, herein we studied a set of two derivatives featuring a different alkylation patterning. The followed synthetic route, involving various sulfurated carbazole-based molecules, also resulted in a source of fluorophores with different emitting behaviors. Surprisingly, the sulfoxide-containing fluorophores substantially increased their blue fluorescence with respect to the nearly non-emitting sulfur counterparts. On this basis, we could shed light on the relationship between their chemical structure and their emission as an approach for future applications. Considering the performance in organic thin-film transistors, both bisbenzothienocarbazole derivatives displayed p-type characteristics, with hole mobility values up to 1.1 × 10−3 cm2 V−1 s−1 and considerable air stability. Moreover, the role of the structural design has been correlated with the device performance by means of X-ray analysis and the elucidation of the corresponding single crystal structures.

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Exploring the 3-(phenylethynyl)-9H-carbazole unit in the search of deep-blue emitting fluorophores

Cited by 3 publications

References 48 publications

Insight into the Diindolo[3,2-b:2′,3′-h]carbazole Core as an Air-Stable Semiconductor for OTFTs

Insight into the Diindolo[3,2-b:2′,3′-h]carbazole Core as an Air-Stable Semiconductor for OTFTs

Programming Positive Mechanofluorescence in Liquid Crystalline Elastomers

Towards the Bisbenzothienocarbazole Core: A Route of Sulfurated Carbazole Derivatives with Assorted Optoelectronic Properties and Applications

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