Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials

Коваленко, А. В.; Yumusak, Cigdem; Heinrichová, Patricie; Stříteský, Stanislav; Fekete, Ladislav; Vala, Martin; Weiter, Martin; Sariciftci, Niyazi Serdar; Krajčovič, Jozef

doi:10.1039/c6tc05076j

Cited by 45 publications

(27 citation statements)

References 53 publications

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“…The crystal structures of Ada‐ 1 and Hex ‐1 single crystals were reported previously [16] . The supramolecular structure of the thin film of Hex ‐1 prepared by vapor deposition method with subsequent solvent annealing was reported in detail in a previous publication [17] .…”

Section: Resultsmentioning

confidence: 96%

“…Crude Ada-1 was crystallized from toluene as described recently. [16] A dark 1 × 1 × 2 mm single crystal of But-1 was prepared by slow cooling of a hot solution in DMF.…”

Section: Methodsmentioning

confidence: 99%

“…For Hex-1, it is higher than the value of 27 Figure 1. Molecular pairs in single-crystal structures of Ada-1 [16] (a,d), But-1 (b,e), and Hex-1 [24] (c,f) shown in face-on (a-c) and edge-on (d-f) projections. The same Ada-1 structure was also found in the SC, VD and VD-SA films, the same But-1 structure was found in the SC film, and the same Hex-1 structure was found in the SC, VD, and VD-SA films.…”

Section: Steady-state Optical Absorption and Fluorescencementioning

confidence: 99%

“…In this report, we present transient optical absorption and fluorescence spectra of three TDPP derivatives (structures R‐ 1 in Scheme 1) containing n ‐hexyl, n ‐butyl, or 2‐(adamant‐1‐yl)ethyl [16] substituents on both N ‐heteroatoms of the conjugated core. We focused on the exciton fission mechanism and found that the SF rate constants are nearly the same for all three compounds.…”

Section: Introductionmentioning

confidence: 99%

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Singlet Fission in Thin Solid Films of Bis(thienyl)diketopyrrolopyrroles

et al. 2020

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The singlet fission (SF) process discovered in bis(thienyl) diketopyrrolopyrroles (TDPPs) can boost their potential for photovoltaics (PV). The crystal structures of TDPP analogs carrying n-hexyl, n-butyl, or 2-(adamant-1-yl)ethyl substituents are similar, but contain increasingly slipped stacked neighbor molecules. The observed SF rate constants, k SF , (7 � 4), (9 � 3) and (5.6 � 1.9) ns À 1 for thin films of the three compounds, respectively, are roughly equal, but the triplet quantum yields vary strongly: (120 � 40), (160 � 40) and (70 � 16), respectively. The recent molecular pair model reproduces the near equality of all three k SF at the crystal geometries and identifies all possible pair arrangements in which SF is predicted to be faster, by up to two orders of magnitude. However, it is also clear that the presently non-existent ability to predict the rates of processes competing with SF is pivotal for providing a guide for efforts to optimize the materials for PV.

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Section: Resultsmentioning

confidence: 96%

“…Crude Ada-1 was crystallized from toluene as described recently. [16] A dark 1 × 1 × 2 mm single crystal of But-1 was prepared by slow cooling of a hot solution in DMF.…”

Section: Methodsmentioning

confidence: 99%

Section: Steady-state Optical Absorption and Fluorescencementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Singlet Fission in Thin Solid Films of Bis(thienyl)diketopyrrolopyrroles

et al. 2020

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“…This can be attributed to a higher degree of self-organization that is common in adamantyl compounds. 39,40 Where: λ max -wavelength at the emission maximum, FWHM -full width at half maximum of the emission peak; E g -optical bandgap.…”

Section: Methodsmentioning

confidence: 99%

Proteinogenic Amino Acid Assisted Preparation of Highly Luminescent Hybrid Perovskite Nanoparticles

Procházková

Demchyshyn

Yumusak

et al. 2019

ACS Appl. Nano Mater.

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Versatile approaches to nanoparticle synthesis offer unprecedented opportunities for the development of optoelectronics, photonics, as well as bio sciences. With the current advancement of hybrid organic-inorganic metal halide perovskites, the next step is to expand their field of applications via utilization of functional and modifiable ligand chemistry. Here, we present a ligand assisted reprecipitation approach for highly luminescent perovskite nanoparticle synthesis using for the first time L-lysine and L-arginine for surface passivation. These nanoparticles exhibit emission within a narrow bandwidth of the visible spectrum and photoluminescence quantum yield close to 100%. Additionally, preferential ligand orientation is achieved via amino acids α-amino group blocking which results in blueshifted emission as well as smaller and more uniform particle size. These experimental results demonstrate the effectiveness of naturally occurring proteinogenic amino acids as surface ligands and offer possibilities for versatile modification of perovskite nanoparticle properties via well-studied amino acid chemistry.

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Adamantyl Substitution Strategy for Realizing Solution‐Processable Thermally Stable Deep‐Blue Thermally Activated Delayed Fluorescence Materials

2018

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Highly efficient solution-processable emitters, especially deep-blue emitters, are greatly desired to develop low-cost and low-energy-consumption organic light-emitting diodes (OLEDs). A recently developed class of potentially metal-free emitters, thermally activated delayed fluorescence (TADF) materials, are promising candidates, but solution-processable TADF materials with efficient blue emissions are not well investigated. In this study, first the requirements for the design of efficient deep-blue TADF materials are clarified, on the basis of which, adamantyl-substituted TADF molecules are developed. The substitution not only endows high solubility and excellent thermal stability but also has a critical impact on the molecular orbitals, by pushing up the lowest unoccupied molecular orbital energy and triplet energy of the molecules. In the application to OLEDs, an external quantum efficiency (EQE) of 22.1% with blue emission having Commission Internationale de l'Eclairage (CIE) coordinates of (0.15, 0.19) is realized. A much deeper blue emission with CIE (0.15, 0.13) is also achieved, with an EQE of 11.2%. These efficiencies are the best yet among solution-processed TADF OLEDs of CIE y < 0.20 and y < 0.15, as far as known. This work demonstrates the validity of adamantyl substitution and paves a pathway for straightforward realization of solution-processable efficient deep-blue TADF emitters.

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Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials

Abstract: Ethyladamantyl solubilization side groups were found to induce π−π interactions between the conjugated cores in soluble diketopyrrolopyrrole derivatives.

Cited by 45 publications

References 53 publications

Singlet Fission in Thin Solid Films of Bis(thienyl)diketopyrrolopyrroles

Singlet Fission in Thin Solid Films of Bis(thienyl)diketopyrrolopyrroles

Proteinogenic Amino Acid Assisted Preparation of Highly Luminescent Hybrid Perovskite Nanoparticles

Adamantyl Substitution Strategy for Realizing Solution‐Processable Thermally Stable Deep‐Blue Thermally Activated Delayed Fluorescence Materials

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