Fluorene-Based Donor-Acceptor Copolymers Containing Functionalized Benzotriazole Units: Tunable Emission and their Electrical Properties

Monomers 4,7-dibromo-2H-benzo[d]1,2,3-triazole (m1) and 4,7-(bis(4-bromophenyl)ethynyl)-2H-benzo[d]1,2,3-triazole (m2) have been synthesized in good yields using different procedures. Monomers m1 and m2 have been employed for building new copolymers of fluorene derivatives by a Suzuki reaction under microwave irradiation using the same conditions. In each case different chain lengths have been achieved, while m1 gives rise to polymers for m2 oligomers have been obtained (with a number of monomer units lower than 7). Special interest has been paid to their photophysical properties due to excited state properties of these D-A units alternates, which have been investigated by density functional theory (DFT) calculations using two methods: (i) An oligomer approach and (ii) by periodic boundary conditions (PBC). It is highly remarkable the tunability of the photophysical properties as a function of the different monomer functionalization derived from 2H-benzo[d]1,2,3-triazole units. In fact, a strong modulation of the absorption and emission properties have been found by functionalizing the nitrogen N-2 of the benzotriazole units or by elongation of the π-conjugated core with the introduction of alkynylphenyl groups. Furthermore, the charge transport properties of these newly synthesized macromolecules have been approached by their implementation in organic field-effect transistors (OFETs) in order to assess their potential as active materials in organic optoelectronics.

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Preparation and Photophysical Properties of All-trans Acceptor–π-Donor (Acceptor) Compounds Possessing Obvious Solvatochromic Effects

Australian Journal of Chemistry ◽

10.1071/ch17021 ◽

2017 ◽

Vol 70 (9) ◽

pp. 1048

Author(s):

Yu-Lu Pan ◽

Zhi-Bin Cai ◽

Li Bai ◽

Sheng-Li Li ◽

Yu-Peng Tian

Keyword(s):

Density Functional Theory ◽

Density Functional ◽

Photophysical Properties ◽

Emission Spectra ◽

Photon Absorption ◽

Linear Absorption ◽

Functional Theory ◽

Two Photon Absorption ◽

Two Photon ◽

Donor Acceptor

A series of all-trans acceptor–π-donor (acceptor) compounds (BAQ, SFQ, BLQ, and XJQ) were conveniently synthesised and characterised by infrared, nuclear magnetic resonance, mass spectrometry, and elemental analysis. Their photophysical properties, including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated. All the compounds show obvious solvatochromic effects, such as significant bathochromic shifts of the emission spectra and larger Stokes shifts in more polar solvents. Under excitation from a femtosecond Ti : sapphire laser with a pulse width of 140 fs, they all exhibit strong two-photon excited fluorescence, and the two-photon absorption cross-sections in THF are 851 (BAQ), 216 (SFQ), 561 (BLQ), and 447 (XJQ) GM respectively. A combination of density functional theory (DFT) and time-dependent density functional theory (TDDFT) approaches was used to investigate the relationships between the structures and the photophysical properties of these compounds. The results show that they may have a potential application as polarity-sensitive two-photon fluorescent probes.

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Semiconductor Performance of Phthalocyaninato Lead Complex and Its Nonperipheral Substituted Derivatives for Organic Field Effect Transistors: Density Functional Theory Calculations

The Journal of Physical Chemistry C ◽

10.1021/jp9113305 ◽

2010 ◽

Vol 114 (7) ◽

pp. 3248-3255 ◽

Cited By ~ 16

Author(s):

Aimin Zhong ◽

Yongzhong Bian ◽

Yuexing Zhang

Keyword(s):

Density Functional Theory ◽

Field Effect ◽

Density Functional ◽

Field Effect Transistors ◽

Density Functional Theory Calculations ◽

Organic Field Effect Transistors ◽

Functional Theory ◽

Lead Complex

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Raman Spectroscopic Studies of Dinaphthothienothiophene (DNTT)

Materials ◽

10.3390/ma12040615 ◽

2019 ◽

Vol 12 (4) ◽

pp. 615 ◽

Cited By ~ 4

Author(s):

Bishwajeet Bhardwaj ◽

Takeshi Sugiyama ◽

Naoko Namba ◽

Takayuki Umakoshi ◽

Takafumi Uemura ◽

...

Keyword(s):

Charge Carrier ◽

Carrier Mobility ◽

Density Functional ◽

Field Effect Transistors ◽

Charge Carrier Mobility ◽

Spectroscopic Studies ◽

Organic Field Effect Transistors ◽

Functional Theory ◽

Raman Spectroscopic ◽

The Density Functional Theory

The application of dinaphthothienothiophene (DNTT) molecules, a novel organic semiconductor material, has recently increased due to its high charge carrier mobility and thermal stability. Since the structural properties of DNTT molecules, such as the molecular density distribution and molecular orientations, significantly affect their charge carrier mobility in organic field-effect transistors devices, investigating these properties would be important. Here, we report Raman spectroscopic studies on DNTT in a transistor device, which was further analyzed by the density functional theory. We also show a perspective of this technique for orientation analysis of DNTT molecules within a transistor device.

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Organic Field-Effect Transistors Based on 3’-Flouro-2,2',6,6'-Tetraphenyl-4,4'-Dipyranylidene

Solid State Phenomena ◽

10.4028/www.scientific.net/ssp.288.37 ◽

2019 ◽

Vol 288 ◽

pp. 37-43

Author(s):

Altan Bolag ◽

Yoshiro Yamashita

Keyword(s):

Field Effect ◽

Density Functional ◽

Field Effect Transistors ◽

Organic Field Effect Transistors ◽

X Ray Diffraction ◽

Si Substrate ◽

Visible Spectroscopy ◽

Functional Theory ◽

X Ray ◽

Contact Configuration

In this work, 3’-flouro-2,2',6,6'-tetraphenyl-4,4'-dipyranylidene (3FDP) was originally synthesized and investigated with density functional theory (DFT) calculations, ultraviolet–visible spectroscopy (UV–Vis) and cyclic voltammetry (CV) in comparison with 2,2',6,6'-tetraphenyl-4,4'-dipyranylidene (DP) and 4’-flouro-2,2',6,6'-tetraphenyl-4,4'-dipyranylidene (4FDP). 3FDP-based organic field-effect transistors (OFETs) were fabricated with bottom contact configuration on bare SiO2/Si substrate, 1,1,1,3,3,3-hexamethyldisilazane (HMDS) and octadecyltrichlorosilane (OTS) treated substrate, respectively. The HMDS-treated device showed highest mobility of 4 × 10−4 cm2 V−1 s−1, on/off ratio of 4 × 103 and threshold voltage of −10 V. Finally, vacuum deposited 3FDP films morphology was investigated by X-ray diffraction (XRD) analyses and the results showed higher crystallinity of HMDS-treated 3FDP film compared to the OTS-treated film, leading to a better FET performance.

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Raman investigation of electric ﬁeld induced molecular modiﬁcations in organic ﬁeld eﬀect transistors

ELEMENTOS ◽

10.15765/e.v2i2.185 ◽

2013 ◽

Vol 2 (2) ◽

Author(s):

Beynor Antonio Paez Sierra ◽

Fredy Giovanni Mesa Rodríguez

Keyword(s):

Electric Field ◽

Electric Fields ◽

Field Effect ◽

Density Functional ◽

Field Effect Transistors ◽

Dipole Interaction ◽

Original Structure ◽

Organic Layer ◽

Organic Field Effect Transistors ◽

Functional Theory

The inﬂuence of external electric ﬁelds on the vibrational properties of Pentacene-based ﬁeld eﬀect transistors were investigated by Ramanspectroscopy.ThemonitoredRamanbandswereintherangefrom 1100cm−1 to1200cm−1,whereabroadbandispresentandenhanceddue to the external electric ﬁeld. The process is modeled by density functional theory (DFT) at the B3LYP/3–21G level. Additionally, the relaxation of the Raman bands after the removal of the external ﬁeld was determined from an exponential Debye like decay ﬁtting to be approximately 94 min, this ﬁnding indicates that a long relaxation time ca. 8 h is required in order to recover the original structure. Experimentally and theoretically was demonstrated that the applied electric ﬁelds induce artiﬁcial traps in the organic layer mediated by charge carrier–dipole interaction.

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Oligofuran–Benzothiadiazole Co-oligomers: Synthesis, Optoelectronic Properties and Reactivity

Organic Materials ◽

10.1055/s-0041-1729853 ◽

2021 ◽

Vol 03 (02) ◽

pp. 303-308

Author(s):

Dror Ben Abba Amiel ◽

Choongik Kim ◽

Ori Gidron

Keyword(s):

Organic Solar Cells ◽

Field Effect ◽

Field Effect Transistors ◽

Organic Light Emitting Diodes ◽

Organic Field Effect Transistors ◽

Active Materials ◽

Light Emitting ◽

Organic Light ◽

Donor Acceptor ◽

Optical Bandgaps

Donor–acceptor–donor (DAD) triad systems are commonly applied as active materials in ambipolar organic field-effect transistors, organic solar cells, and NIR-emitting organic light-emitting diodes. Often, these triads utilize oligothiophenes as donors, whereas their oxygen-containing analogs, oligofurans, are far less studied in this setup. Here we introduce a family of DAD triads in which the donors are oligofurans and the acceptor is benzothiadiazole. In a combined computational and experimental study, we show that these triads display optical bandgaps similar to those of their thiophene analogs, and that a bifuran donor is sufficient to produce emission in the NIR spectral region. The presence of a central acceptor unit increases the photostability of oligofuran-based DAD systems compared with parent oligofurans of the similar length.

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Photophysical Properties of N-Methyl and N-Acetyl Substituted Alloxazine: A Theoretical Investigation

Physical Chemistry Chemical Physics ◽

10.1039/d1cp01201k ◽

2021 ◽

Author(s):

Huimin Guo ◽

Xiaolin Ma ◽

Zhiwen Lei ◽

Yang Qiu ◽

Bernhard Dick ◽

...

Keyword(s):

Density Functional Theory ◽

Electronic Structure ◽

Theoretical Investigation ◽

Density Functional ◽

Photophysical Properties ◽

Time Dependent ◽

Functional Theory ◽

Td Dft ◽

Dependent Density

The electronic structure and photophysical properties of a series of N-Methyl and N-Acetyl substituted alloxazine (AZs) were investigated with extensive density functional theory (DFT) and time-dependent density functional theory (TD-DFT)...

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Time-Dependent Density-Functional Theory Investigation of the Fluorescence Behavior as a Function of Alkyl Chain Size for the 4-(N,N-Dimethylamino)benzonitrile-like Donor−Acceptor Systems 4-(N,N-Diethylamino)benzonitrile and 4-(N,N-Diisopropylamino)benzonitrile

The Journal of Physical Chemistry B ◽

10.1021/jp0307699 ◽

2004 ◽

Vol 108 (22) ◽

pp. 7132-7141 ◽

Cited By ~ 37

Author(s):

Christine Jödicke Jamorski ◽

Mark E. Casida

Keyword(s):

Density Functional Theory ◽

Density Functional ◽

Alkyl Chain ◽

Time Dependent ◽

Functional Theory ◽

Donor Acceptor ◽

Dependent Density

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Anthracene Based AIE Active Probe for Colorimetric and Fluorimetric Detection of Cu2+ Ions

Zeitschrift für Physikalische Chemie ◽

10.1515/zpch-2018-1215 ◽

2019 ◽

Vol 233 (7) ◽

pp. 895-911 ◽

Cited By ~ 1

Author(s):

Abdullah G. Al-Sehemi ◽

Ahmad Irfan ◽

Mehboobali Pannipara ◽

Mohammed A. Assiri ◽

Abul Kalam

Keyword(s):

Charge Transfer ◽

Density Functional ◽

Photophysical Properties ◽

Functional Theory ◽

Water Fraction ◽

Cu Complex ◽

Active Probe ◽

And Function ◽

Intra Molecular Charge Transfer ◽

Metal Charge Transfer

Abstract A novel aggregation induced emission (AIE) active anthracene based dihydroquinazolinone derivative (probe 1) has been synthesized and characterized by means of spectroscopic methods. The photophysical properties of this probe have been investigated in solvents of different polarity display that fluorescence states are of intramolecular charge transfer (ICT) character. Probe 1 show clear AIE behavior in water/THF mixture on reaching water fraction 95%. The AIE behavior of probe 1 have been exploited for the detection of metal ions in aqueous solution which reveals high selectivity and sensitivity towards Cu2+ ions by colorimetrically and function as a chemosensor in a remarkable turn-off fluorescence manner. Further, the experimental results were investigated by computational means by optimizing the ground state geometries of probe 1 and probe 1-Cu complex using density functional theory (DFT) at B3LYP/6-31G∗∗ and B3LYP/6-31G∗∗(LANL2DZ) levels of theory. Intra-molecular charge transfer was observed in probe 1 while ligand to metal charge transfer (LMCT) for probe 1-Cu complex.

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Wechselwirkungen in Molekülkristallen, 166 [1, 2]. Polyiod-Moleküle I2C=CI2, (IC)4S, (IC)4NH, (IC)4N-CH3 und HCI3: Strukturbestimmung nach Kristallzüchtung oder durch Dichtefunktionaltheorie-Berechnung / Interaction in Molecular Crystals, 166 [1, 2], Polyiodo Molecules I2C=CI2, (IC)4S, (IC)4 NH, (IC)4N-CH and HCI3: Structure Determination Following Crystallization or by Density Functional Theory Calculation

Zeitschrift für Naturforschung B ◽

10.1515/znb-2001-0104 ◽

2001 ◽

Vol 56 (1) ◽

pp. 13-24 ◽

Cited By ~ 4

Author(s):

Hans Bock ◽

Sven Holl ◽

Volker Krenzel

Keyword(s):

Density Functional Theory ◽

Density Functional ◽

Crystal Packing ◽

Density Functional Theory Calculation ◽

Density Functional Theory Calculations ◽

Structural Data ◽

Basis Sets ◽

Functional Theory ◽

Donor Acceptor ◽

Density Functional Theory Optimization

Abstract The structures of tri-and tetraiodo-substituted carbon compounds are determined either experimentally by X-Ray Structure Analysis or, because crystallization of tetraiodothiophene could not be achieved, approximated by Density Functional Theory optimization of structural data from a donor/acceptor complex. The structures show noteworthy details such as a second polymorph of tetraiodoethene crystallized by sublimation or herringbone crystal packing patterns of tetraiodopyrrole derivatives. All molecular geometries are discussed and compared based on relativistic density functional theory calculations with 6 -31G* basis sets including iodine pseudopotentials. They reproduce even finer structural details due to van der Waals repulsion of the bulky iodo substituents. Natural Bond Orbital (NBO) charge distributions suggest positive partial charges at all iodine centers with the strongest polarization Cδ㊀ → Iδ㊉ in HCI3, which contains well over 97% iodine.

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