V-shaped pyranylidene/triphenylamine-based chromophores with enhanced photophysical, electrochemical and nonlinear optical properties

Gámez‐Valenzuela, Sergio; Neußer, David; Benítez-Martín, Carlos; Nájera, Francisco; Guadix, Juan Antonio; Moreno–Yruela, Carlos; Villacampa, Belén; Ortiz, Rocío Ponce; Ludwigs, Sabine; Andreu, Raquel; Delgado, M. Carmen Ruiz

doi:10.1039/d1ma00415h

Cited by 6 publications

(4 citation statements)

References 60 publications

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“…The second enhances the fluorescent properties and favours red-shifting. [20][21][22] Both groups are linked by an alkynyl group, which favours the formation of supramolecular structures due to its ability to generate CÀ H•••π interactions as previously observed by our research group. [23,24] Finally, in order to improve the processability in photonic and electronic devices and to avoid future solubility problems, a six-carbons alkyl chain was introduced in the thiophene ring.…”

Section: Introductionmentioning

confidence: 52%

“…The first possesses high donor character and an excellent charge transport capacity, [19] improving its applicability as semiconductor. The second enhances the fluorescent properties and favours red‐shifting [20–22] . Both groups are linked by an alkynyl group, which favours the formation of supramolecular structures due to its ability to generate C−H⋅⋅⋅π interactions as previously observed by our research group [23,24] .…”

Section: Introductionmentioning

confidence: 53%

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Rational Design of a Multifunctional Benzothiadiazole Derivative in Organic Photonics and Electronics

Tardío,

Donoso,

Fernández

et al. 2023

Chemistry A European J

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In order to achieve a multifunctional compound with potential application in organic photonics and electronics, a multidonor benzothiadiazole derivative was rationally designed and synthesized employing microwave irradiation as energy source, increasing the process efficiency about yields and reaction times in comparison with conventional conditions. This powerful compound displayed solvatochromism and showed efficient behavior as red optical waveguide with low OLC around 10‐2 dB μm‐1 and with the capacity of light transmission in two directions. In addition, the proposed derivative acted as efficient p‐type semiconductor in organic field‐effect transistors (OFETs) with hole mobilities up 10‐1 cm2V‐1s‐1. This corroborates its multifunctional character, thus making it a potential candidate to be applied in hybrid organic field‐effect optical waveguides (OFEWs).

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Section: Introductionmentioning

confidence: 52%

Section: Introductionmentioning

confidence: 53%

Rational Design of a Multifunctional Benzothiadiazole Derivative in Organic Photonics and Electronics

Tardío,

Donoso,

Fernández

et al. 2023

Chemistry A European J

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“…Among them, push-pull chromophores (referred to classically as donor-π-bridge-acceptors or D-π-A) are a class of peculiar importance [56] with various shapes, such as linear, branched, twisted, planar, nonplanar, etc. [57,58], exhibiting linear and/or nonlinear optical properties and electrical properties that are useful, for instance, in the design, conception, and manufacture of electronic devices. These molecules typically consist of an electron-donating (push) unit and an electron-withdrawing (pull) unit connected through a conjugated bridge (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Self-Assembled Monolayers of Push–Pull Chromophores as Active Layers and Their Applications

Wang,

Gadenne,

Patrone

et al. 2024

Molecules

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In recent decades, considerable attention has been focused on the design and development of surfaces with defined or tunable properties for a wide range of applications and fields. To this end, self-assembled monolayers (SAMs) of organic compounds offer a unique and straightforward route of modifying and engineering the surface properties of any substrate. Thus, alkane-based self-assembled monolayers constitute one of the most extensively studied organic thin-film nanomaterials, which have found wide applications in antifouling surfaces, the control of wettability or cell adhesion, sensors, optical devices, corrosion protection, and organic electronics, among many other applications, some of which have led to their technological transfer to industry. Nevertheless, recently, aromatic-based SAMs have gained importance as functional components, particularly in molecular electronics, bioelectronics, sensors, etc., due to their intrinsic electrical conductivity and optical properties, opening up new perspectives in these fields. However, some key issues affecting device performance still need to be resolved to ensure their full use and access to novel functionalities such as memory, sensors, or active layers in optoelectronic devices. In this context, we will present herein recent advances in π-conjugated systems-based self-assembled monolayers (e.g., push–pull chromophores) as active layers and their applications.

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“…The novelty of using the pyran moiety as a donor unit for the application in 2PLP is worth noting. 2PA activity has been reported for some pyran derivatives [ 27,28 ] featuring mainly this moiety as π ‐spacer [ 29 ] but, the potential of this donor moiety as 2PLP PIs has, to the best of our knowledge, not been investigated before.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Photoninitiators Based on 4H‐Pyranylidene Derivatives for Two‐Photon Laser Printing

Royo

Mainik

Benítez-Martín

et al. 2023

Adv Materials Technologies

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A series of four donor–acceptor–donor derivatives bearing 4H‐pyranylidene and 4‐methylcyclohexan‐1‐one units as donor and acceptor groups respectively is designed, synthesized, and photophysically characterized. Both experimental and theoretical studies reveal good two‐photon absorption (2PA) properties for these systems. Decoration of the exocyclic position of the 4H‐pyranylidene moiety with a thiophene ring results in high 2PA cross‐section values (σ2PA) ≈700 nm, and remarkably, in the region between 900 and 1000 nm. Furthermore, all chromophores are evaluated as photoinitiators (PIs) for two‐photon‐laser printing at 780 nm, showing superior performance compared to the commonly used commercially available PI, phenylbis(2,4,6‐trimethylbenzoyl)phosphine oxide. Among the studied PIs, the ones equipped with a thiophene unit at the exocyclic position of the 4H‐pyranylidene moiety exhibit the highest efficiency, enabling fast printing using low laser powers with even lower concentrations of PI. Overall, this study shows the great potential of this new class of PIs for application in the field of 3D nanoprinting.

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V-shaped pyranylidene/triphenylamine-based chromophores with enhanced photophysical, electrochemical and nonlinear optical properties

Abstract: We report the synthesis and comprehensive study of two chromophores based on 4H-pyranylidene moiety as a part of the π-conjugated spacer. Triphenylamine (TPA) acts as donor and tricarbonitrile-based electron-accepting groups...

Cited by 6 publications

References 60 publications

Rational Design of a Multifunctional Benzothiadiazole Derivative in Organic Photonics and Electronics

Rational Design of a Multifunctional Benzothiadiazole Derivative in Organic Photonics and Electronics

Self-Assembled Monolayers of Push–Pull Chromophores as Active Layers and Their Applications

Highly Efficient Photoninitiators Based on 4H‐Pyranylidene Derivatives for Two‐Photon Laser Printing

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