Synthesis and investigation on liquid crystal and optical properties of dyads based on triphenylene and perylene

Kong, Xiangfei; Xia, Liting; Zhang, Haifeng; Dai, Shengping; Yu, Caili; Liu, Zheng; Mu, Linping; Wang, Guixia; He, Zhengjie

doi:10.1039/c7ra01320e

Cited by 13 publications

(14 citation statements)

References 45 publications

(32 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this subsection, the last developments regarding the synthesis of novel discotic mesogenic materials will be described. Triphenylene derivatives still remain the most studied compounds and they have been used to develop new materials, testing new side chains, or new cores [ 191 , 192 , 193 , 194 , 195 , 196 ], to be linked with other cores to prepare dyads and triads [ 67 , 197 , 198 , 199 , 200 ] or materials giving segregate columns [ 201 , 202 ]. Triphenylenes were also doped with nanoparticles or used to prepare blends with other mesogenic molecules [ 203 , 204 , 205 ].…”

Section: Recent Advances In the Study Of Discotic Liquid Crystalsmentioning

confidence: 99%

“…Triphenylene was also used as a constituent of dyads and triads, often in molecular system in which an electron donor (D) is covalently linked to an electron acceptor (A), with the aim of obtaining a “molecular heterojunction” [ 168 , 197 , 198 , 200 , 206 , 207 ]. This kind of molecular system can be a good candidate to produce optoelectronic devices, such as organic light-emitting diodes (OLED) and organic solar cells (OSC).…”

Section: Recent Advances In the Study Of Discotic Liquid Crystalsmentioning

confidence: 99%

See 1 more Smart Citation

Charge Mobility in Discotic Liquid Crystals

Termine

Golemme

2021

IJMS

View full text Add to dashboard Cite

Discotic (disk-shaped) molecules or molecular aggregates may form, within a certain temperature range, partially ordered phases, known as discotic liquid crystals, which have been extensively studied in the recent past. On the one hand, this interest was prompted by the fact that they represent models for testing energy and charge transport theories in organic materials. However, their long-range self-assembling properties, potential low cost, ease of processability with a variety of solvents and the relative ease of tailoring their properties via chemical synthesis, drove the attention of researchers also towards the exploitation of their semiconducting properties in organic electronic devices. This review covers recent research on the charge transport properties of discotic mesophases, starting with an introduction to their phase structure, followed by an overview of the models used to describe charge mobility in organic substances in general and in these systems in particular, and by the description of the techniques most commonly used to measure their charge mobility. The reader already familiar or not interested in such details can easily skip these sections and refer to the core section of this work, focusing on the most recent and significant results regarding charge mobility in discotic liquid crystals.

show abstract

Section: Recent Advances In the Study Of Discotic Liquid Crystalsmentioning

confidence: 99%

Section: Recent Advances In the Study Of Discotic Liquid Crystalsmentioning

confidence: 99%

Charge Mobility in Discotic Liquid Crystals

Termine

Golemme

2021

IJMS

View full text Add to dashboard Cite

show abstract

“…Thus, the LUMO values of TPPE and PIE3 were -3.64 and -3.65 eV, respectively. As we know, the LUMO of a dyad linked by a flexible spacer is coincident with the lower one of the two units [30]. Thus, the HOMO value (-5.95 eV), corresponding to E ox (2), and E g (2.30 eV) of perylene unit should be used in the equation LUMO = HOMO + E g , and the LUMO value of TPP-C 10 -PIE is -3.65 eV.…”

Section: Electrochemical Behaviors and Homo/lumo Energy Levelsmentioning

confidence: 99%

“…In addition, the potential value of the dyad corresponding to the onset of the second oxidation wave (denoted by E ox (2)) was 1.59 V. Analysis of these data showed that the first and second oxidation waves of the dyads can be assigned to the oxidation reactions of the porphyrin unit and the perylene unit, respectively. The LUMO value of a compound can be estimated from the optical band gap (denoted as E g ) and the HOMO value by the equation LUMO = HOMO + E g [30]. The E g was inferred from the onset of the longest wavelength absorption band.…”

Section: Electrochemical Behaviors and Homo/lumo Energy Levelsmentioning

confidence: 99%

See 1 more Smart Citation

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Kong

Gong

Dai

et al. 2018

J. Porphyrins Phthalocyanines

Self Cite

View full text Add to dashboard Cite

Five novel dyads, consisting of a tetraphenylporphyrine unit connected to a perylene monoimide diester unit via a flexible bridge -CONH-(CH 2 ) n -(n = 4, 6, 8, 10 and 12), have been synthesized. Their structures were characterized by 13 C and 1 H nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry and elemental analysis. The UV-vis absorption spectra revealed these dyads have broad optical absorption in the ultraviolet and visible regions due to the complementary absorption of the two units. The differential scanning calorimetry traces and polarized optical microscopy textures showed all these dyads have columnar liquid crystal phases. Cyclic voltammetry revealed the highest occupied molecular orbitals of the dyads located on the porphyrin units, and the lowest unoccupied molecular orbitals located on the perylene units. In addition, these results were in agreement with that of the theoretical modeling. When excited at 423 or 473 nm, the photoluminescent emission spectra showed that the degree of fluorescence quenching of porphyrin units increased as the spacers became shorter. This quenching was ascribed to intramolecular photoinduced electron transfer, which also induced the dyad molecules to form the charge-separated states. The charge-separated molecules were further confirmed by the photocurrent response curves. These behaviors of broad absorption of the ultraviolet-visible light, yielding the charge-separated states of the molecules when excited and the formation of columnar liquid crystal phase made these dyads candidates for single-component photovoltaic active materials.

show abstract

Transparent Liquid Crystal Hole‐Transporting Material for Stable Perovskite Solar Cells

et al. 2022

View full text Add to dashboard Cite

Hexakis(hexyloxy)triphenylene (HAT6) discotic liquid crystal is employed as a transparent hole‐transporting material (HTM) for perovskite solar cells (PSCs) and a power conversion efficiency (PCE) of 15.7% is obtained, which is the highest using HAT6 type of HTMs. Despite lower PCE than spiro‐OMeTAD‐based devices (20.3%), the PSCs based on HAT6 exhibit much higher ambient and thermal stability. A fused polyaromatic core with six alkyl chains leads to high hydrophobicity, and the π‐stacked molecular columns of the HAT6 shield the bis(trifluoromethane)sulfonamide lithium salt dopant migration into the perovskite absorber. The PSCs (under N2 condition) exhibit superior stability compared to the devices employing spiro‐OMeTAD, retaining nearly 92% of their initial efficiency after 1200 h operation. Under ambient conditions, HAT6‐based hole‐transportation layer devices retain 93% of the initial efficiency for 690 h. Under continuous thermal stress of 85 °C, the devices based on HAT6 retain 95% of the initial PCE. The results demonstrate the time applicability of liquid crystal for stable PSCs fabrication.

show abstract

Synthesis and investigation on liquid crystal and optical properties of dyads based on triphenylene and perylene

Abstract: Mesogenic dyads consisting of a triphenylene (donor) and a perylene (acceptor) showed photoinduced intramolecular charge transfer process and fluorescent quenching.

Cited by 13 publications

References 45 publications

Charge Mobility in Discotic Liquid Crystals

Charge Mobility in Discotic Liquid Crystals

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Transparent Liquid Crystal Hole‐Transporting Material for Stable Perovskite Solar Cells

Contact Info

Product

Resources

About