Croconaines as molecular materials for organic electronics: synthesis, solid state structure and use in transistor devices

Punzi, Angela; Capozzi, Maria Annunziata M.; Fino, V.; Carlucci, Claudia; Suriano, M.; Mesto, Ernesto; Schingaro, Emanuela; Orgiu, Emanuele; Bonacchi, Sara; Leydecker, Tim; Samorı́, Paolo; Musio, Roberta; Farinola, Gianluca M.

doi:10.1039/c6tc00264a

Cited by 24 publications

(36 citation statements)

References 23 publications

(7 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…17,18 Alternatively, in very few reported cases, water-insoluble DPP molecules have been processed as nanoparticles with reduced ACQ effect, for application in in vitro and in vivo bioimaging. 16,19 In this context , and following our previous works on development of organometallic protocols for functionalized conjugated structures, [20][21][22][23][24] we recently published a study on the self-assembly process of several amphiphilic red-emitting DPP derivatives, with the formation of H-and Jaggregates in thin-films and organic nanoparticles (ONPs). 25 Unfortunately, upon dispersion in water, all these molecules show a severe ACQ effect, due to the intense π-π stacking of the rigid conjugated structures.…”

Section: Introductionmentioning

confidence: 98%

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Ardizzone

Blasi

Vona

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

Diketopyrrolopyrroles (DPPs) have recently attracted much interest as very bright and photostable red-emitting molecules. However, their tendency to form nonfluorescent aggregates in water through the aggregation-caused quenching (ACQ) effect is a major issue that limits their application under the microscope. Herein, two DPP molecules have been incorporated into the membrane of highly stable and water-soluble quatsomes (QS; nanovesicles composed of surfactants and sterols), which allow their nanostructuration in water and, at the same time, limits the ACQ effect. The obtained fluorescent organic nanoparticles showed superior structural homogeneity, along with long-term colloidal and optical stability. A thorough one- (1P) and two-photon (2P) fluorescence characterization revealed the promising photophysical features of these fluorescent nanovesicles, which showed a high 1P and 2P brightness. Finally, the fluorescent QSs were used for the in vitro bioimaging of Saos-2 osteosarcoma cell lines; this demonstrates their potential as nanomaterials for bioimaging applications.

show abstract

Section: Introductionmentioning

confidence: 98%

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Ardizzone

Blasi

Vona

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Type 16 croconaines have consistently been prepared in refluxing butanol/toluene mixtures over a short period of time (≤ 2 h), either with an inert atmosphere (Ar, [72,78] N 2 [80] ) or without; [27,66] none with the azeotropic removal of water (Scheme 19).…”

Section: Synthesismentioning

confidence: 99%

“…[80] In fact, the X-ray crystal structure of Figure 2. [80] In fact, the X-ray crystal structure of Figure 2.…”

Section: Molecular Structurementioning

confidence: 99%

“…Chem. [72,74,[78][79][80] The first of these is for a type 16 croconaine dye, [72] in which two cis-configurational isomers are possible (Figure 4). Both known croconaine structures are type 4 molecules (R 1 = H) and are shown in Figure 2.…”

Section: Molecular Structurementioning

confidence: 99%

“…Solution fluorescence was reported for type 4 croconaines (R 1 = H) in two papers [78,80] and once for a type 16 croconaine and the corresponding type 31 rotaxane. [74] [60] [c] Type 13 croconaine (R 1 and R 2 = C 12 H 25 ; shown in Scheme 18).…”

mentioning

confidence: 99%

See 2 more Smart Citations

Croconaine Dyes – the Lesser Known Siblings of Squaraines

Lynch

Hamilton

2017

Eur J Org Chem

View full text Add to dashboard Cite

In the 50+ years since the first squaraine dye, made by using 3,4‐dihydroxycyclobut‐3‐ene‐1,2‐dione (squaric acid), was reported, numerous analogues have not only been made and published, but similarly, a number of good review articles on squaraine dyes has also been published. In contrast, for the majority of this time, reports of croconaine dyes, made by using 4,5‐dihydroxy‐4‐cyclopentene‐1,2,3‐trione (croconic acid), have also been published, but they have not received the same attention as squaraine dyes. Furthermore, the only known review of croconaine dyes, which was recently published, is written in Chinese. This current review aims to document the history of croconaine dyes since their first report in a German patent in 1970. This review sources both the scientific literature and published patents, and attention is given to both synthesis and spectroscopic details.

show abstract

Synthetic Routes to Thiol‐Functionalized Organic Semiconductors for Molecular and Organic Electronics

2016

View full text Add to dashboard Cite

Over the few last decades, the potential of using thiol functionalities to induce the self‐assembly of various kinds of molecules on metal surfaces has been widely demonstrated. In particular, π‐conjugated molecules can undergo self‐assembly on metallic surfaces to create electroactive supramolecular layers, which have found important applications in organic and molecular electronics. For this reason, the synthesis of thiol‐functionalized conjugated molecules has been the object of extensive research and many routes have been developed for their synthesis. This Focus Review provides an overview of the state‐of‐the‐art methods for the syntheses of organic semiconductors that are decorated with pendant thiol groups for applications in self‐assembly and molecular and organic electronics. Particular attention is given to synthetic strategies based on organometallic cross‐coupling reactions for the preparation of compounds with extended conjugation.

show abstract

Croconaines as molecular materials for organic electronics: synthesis, solid state structure and use in transistor devices

Abstract: Indolenine-based croconaines are synthesized, their structure and solid state organization are investigated together with their electronic properties in thin-film transistors.

Cited by 24 publications

References 23 publications

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Croconaine Dyes – the Lesser Known Siblings of Squaraines

Synthetic Routes to Thiol‐Functionalized Organic Semiconductors for Molecular and Organic Electronics

Contact Info

Product

Resources

About