Synthesis, Characterization, and Thin-Film Transistor Response of Benzo[i]pentahelicene-3,6-dione

Bracciale, Maria Paola; Kwon, Guhyun; Ho, Dongil; Kim, Choongik; Santarelli, María Laura; Marrocchi, Assunta

doi:10.3390/molecules27030863

Cited by 2 publications

(2 citation statements)

References 93 publications

(91 reference statements)

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“…The investigation of various helicene molecules has attracted significant attention owing to their unusual chiroptical properties and a wide prospect of application in many fields including optoelectronic devices such as organic light-emitting diode and organic field-effect transistor [ 19 , 20 , 21 , 22 , 23 ]. In particular, interest has been aroused in the imaging of stereochemical recognition of carbohelicene molecules on metal surfaces at molecular scale using STM to better understand the fundamental rules responsible for racemate and conglomerate crystallization [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Light Emission from M-Type Enantiomer of 2,13-bis(hydroxymethyl)[7]-thiaheterohelicene Molecules Adsorbed on Au(111) and C60/Au(111) Surfaces Investigated by STM-LE

Krukowski

Hattori

Akai‐Kasaya

et al. 2022

IJMS

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Light emission from the M-type enantiomer of a helicene derivative (2,13-bis(hydroxymethyl)[7]-thiaheterohelicene) adsorbed on the clean Au(111) and the C60-covered Au(111) surfaces were investigated by tunneling-current-induced light-emission technique. Plasmon-originated light emission was observed on the helicence/Au(111) surface and it was strongly suppressed on the area where the helicene molecules were adsorbed at the edges of the Au(111) terraces. To avoid luminescence quenching of excited helicene molecules and to suppress strong plasmon light emission from the Au(111) surface, C60 layers were used as decoupling buffer layers between helicene molecules and the Au(111) surface. Helicene molecules were adsorbed preferentially on the Au(111) surface rather than on the C60 buffer layers due to the small interaction of the molecules and C60 islands. This fact motivated us to deposit a multilayer of helicene molecules onto the C60 layers grown on the Au(111) surface, leading to the fact that the helicene/C60 multilayer showed strong luminescence with the molecules character. We consider that such strong light emission from the multilayer of helicene molecules has a plasmon origin strongly modulated by the molecular electronic states of (M)-[7]TH-diol molecules.

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Section: Introductionmentioning

confidence: 99%

Light Emission from M-Type Enantiomer of 2,13-bis(hydroxymethyl)[7]-thiaheterohelicene Molecules Adsorbed on Au(111) and C60/Au(111) Surfaces Investigated by STM-LE

Krukowski

Hattori

Akai‐Kasaya

et al. 2022

IJMS

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“…Functional organic materials [ 1 ] have become increasingly important in many different fields of application, such as electronics [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ], biomedicine [ 14 , 15 , 16 , 17 , 18 , 19 ], and analytics [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. A rational design allows for the tailoring of the molecular property and applicability of these molecular materials [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

Amphipolar, Amphiphilic 2,4-diarylpyrano[2,3-b]indoles as Turn-ON Luminophores in Acidic and Basic Media

et al. 2022

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A versatile amphiphilic pyrano[2,3-b]indole for halochromic turn-ON luminescence in acidic or basic media is accessed by an insertion-coupling-cycloisomerization and adjusting solubilizing and phenolic functionalities. While almost non-emissive in neutral solutions, treatment with acids or bases like trifluoroacetic acid (TFA) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) reveals distinct luminescence at wavelengths of 540 nm or 630 nm in propan-2-ol, respectively. Turn-ON emission can be detected at pH values as mild as pH = 5.31 or 8.70. Quantum yields in propan-2-ol are substantial for protonated (Φf = 0.058) and deprotonated (Φf = 0.059) species. Photometrically, pKa1 of 3.5 and pKa2 of 10.5 were determined in propan-2-ol. With lipophilic polyether sidechains and hydrophilic protonation and deprotonation sites the molecule can be regarded as amphipolar, which results in good solubility properties for different organic solvents. In aqueous media, an organic co-solvent like propan-2-ol (35%) or tetrahydrofuran (25%) is needed, and the solution can be diluted with pure water without precipitation of the compound. At higher concentrations of water, a turbid solution is formed, which indicates the formation of micellar structures or clusters. With dynamic light scattering we could show that these clusters increase in size with increasing water content.

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Synthesis, Characterization, and Thin-Film Transistor Response of Benzo[i]pentahelicene-3,6-dione

Cited by 2 publications

References 93 publications

Light Emission from M-Type Enantiomer of 2,13-bis(hydroxymethyl)[7]-thiaheterohelicene Molecules Adsorbed on Au(111) and C60/Au(111) Surfaces Investigated by STM-LE

Light Emission from M-Type Enantiomer of 2,13-bis(hydroxymethyl)[7]-thiaheterohelicene Molecules Adsorbed on Au(111) and C60/Au(111) Surfaces Investigated by STM-LE

Amphipolar, Amphiphilic 2,4-diarylpyrano[2,3-b]indoles as Turn-ON Luminophores in Acidic and Basic Media

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