Synthesis, characterization and near infra-red properties of perylenebisimide derivatives

Mazhar, Majid; Abdouss, Majid; Gharanjig, Kamaladin; Teimuri‐Mofrad, Reza

doi:10.1016/j.porgcoat.2016.08.018

Cited by 26 publications

(47 citation statements)

References 19 publications

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“…This behavior suggests that Pigment Red 179 could also behave as an NIR reflective molecule, in agreement with certain symmetrically substituted perylene derivatives. 11…”

Section: Resultsmentioning

confidence: 99%

Aggregation Effects on Pigment Coatings: Pigment Red 179 as a Case Study

Muniz‐Miranda

Minei

Contiero³

et al. 2019

ACS Omega

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Here, we have studied, with a combined experimental and computational approach, the effect of the crystal environment and aggregation on the electronic properties of Pigment Red 179, which affect both its color and optical energy gap. Spectra acquired in the near-infrared and visible range of energies suggest that this molecule is indeed a “cool” dye, which can be employed as a red pigment that provides effective color coverage to different substrates without contributing to their heating during light irradiation. Spectra acquired on different polymer mixtures at different pigment concentrations (i.e., 2.5–10 wt %) suggest that absorption features depend on chromophoric arrangements promoted by the strong intermolecular π–π interactions. Calculations, performed at the time-dependent density functional theory level, allowed to both attribute the nature of the electronic transitions causing the observed spectra involved and understand the effect of the environment. Indeed, the visible spectra of the pigment is dominated by two localized transitions, with negligible charge transfer for both a dye monomer and dimer either in vacuum or acetonitrile solution. Instead, models including the crystal environment of the pigment show the presence of a high-wavelength S1 ← S0 charge transfer transition between two adjacent molecules, in quantitative agreement with the experimental absorption energy of the crystal pigment.

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“…This behavior suggests that Pigment Red 179 could also behave as an NIR reflective molecule, in agreement with certain symmetrically substituted perylene derivatives. 11…”

Section: Resultsmentioning

confidence: 99%

Aggregation Effects on Pigment Coatings: Pigment Red 179 as a Case Study

Muniz‐Miranda

Minei

Contiero³

et al. 2019

ACS Omega

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“…To increase the reaction rate, a range of solid additives [Zn(OAc) 2 ⋅2 H 2 O, CaCl 2 ⋅2 H 2 O, NaHCO 3 , Na 2 CO 3 , K 2 CO 3 ] were screened in the beat and heat method. These additives could act as Lewis acids, dehydration reagents, and/or bases, which could potentially facilitate the condensation reaction . Pleasingly, we found that the addition of inorganic bases such as Na 2 CO 3 and K 2 CO 3 significantly accelerated the consumption of the PTCDA (see Table S3 and Figure S4).…”

Section: Resultsmentioning

confidence: 80%

Greener Dye Synthesis: Continuous, Solvent‐Free Synthesis of Commodity Perylene Diimides by Twin‐Screw Extrusion

et al. 2020

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A continuous, scalable, and solvent‐free method for the synthesis of various naphthalic imides and perylene diimides (PDIs) using twin‐screw extrusion (TSE) is reported. Using TSE, naphthalic imides were obtained quantitatively without the need for excess amine reactant or product purification. With good functional‐group tolerance, alkyl and benzyl amine derived PDIs (incl. commercial dyes) were obtained in 50–99 % yield. Use of K2CO3, enabled synthesis of more difficult aniline‐derived PDIs. Furthermore, an automated continuous TSE process for Pigments Black 31 and 32 is demonstrated, with a throughput rate of about 1500 g day−1, corresponding to a space time yield of about 30×103 kg m−3 day−1, which is 1–2 orders of magnitude greater than for solvent‐based batch methods. These methods provide substantial waste reductions and improved efficiency compared to conventional solvent‐based methods.

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“…The function of plants to reflect solar energy is substituted with the heat‐accumulation effect of the surfaces of these manmade structures. Such an effect, arising from the indiscriminate destruction of natural vegetation, is known as “urban heat island” . This phenomenon is mainly caused by near–infrared (NIR) heat radiation (700–2500 nm) from sunlight .…”

Section: Methodsmentioning

confidence: 99%

Thiophene‐Fused‐Heteroaromatic Diones as Promising NIR Reflectors for Radiative Cooling

et al. 2018

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Developing appropriate NIR‐reflective materials to combat near–infrared (NIR) heat radiation (700–2500 nm) from sunlight, avoiding energy accumulation and reduce energy consumption, is important and highly desirable. In this research, four thiophene‐fused‐heteroaromatic diones were used as basic reflectors to investigate the relationship between their intrinsic molecular structures and NIR‐reflective properties. The reflectance intensity can be readily tuned by adjusting the length of the appended aliphatic side chains, as well as the strength of the electron‐donating groups. A methoxy‐substituted thiophene‐fused‐heteroaromatic dione showed the best performance in reflecting NIR, and it was used as a coating for a model glass house. The comparison of the internal temperature difference relative to a control house was measured and the maximum temperature was 12 °C lower than that in the control house.

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Synthesis, characterization and near infra-red properties of perylenebisimide derivatives

Cited by 26 publications

References 19 publications

Aggregation Effects on Pigment Coatings: Pigment Red 179 as a Case Study

Aggregation Effects on Pigment Coatings: Pigment Red 179 as a Case Study

Greener Dye Synthesis: Continuous, Solvent‐Free Synthesis of Commodity Perylene Diimides by Twin‐Screw Extrusion

Thiophene‐Fused‐Heteroaromatic Diones as Promising NIR Reflectors for Radiative Cooling

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