A new donor for charge-transfer systems: synthesis and properties of 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of (TMDTP)3(PF6)2·2THF and TMDTP–TCNQ

Bendix, Jesper; Bechgaard, K.; Christensen, Jørn B.

doi:10.1039/d1ra00587a

Cited by 3 publications

(4 citation statements)

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“…42,90,100–102 However, such TTF-based OSCs are usually difficult to maintain long-term air stability due to their low ionisation potential of about 4.8 eV. 103–106 Meanwhile, highly conducting CT complexes/salts have been reported even for non-TTF-type donors, such as perylene 107–112 and fluoranthene, 113–116 dithiapyrene, 117–123 and chalcogen-bridged acenes, 124–136 but the transistor properties of these donors are still limited. 137–144 This section describes a new class of non-TTF-based organic conductors derived from high-performance OSC materials.…”

Section: Organic Conductors Based On Organic Semiconductorsmentioning

confidence: 99%

“…42,90,[100][101][102] However, such TTF-based OSCs are usually difficult to maintain long-term air stability due to their low ionisation potential of about 4.8 eV. [103][104][105][106] Meanwhile, highly conducting CT complexes/salts have been reported even for non-TTF-type donors, such as perylene [107][108][109][110][111][112] and fluoranthene, [113][114][115][116] dithiapyrene, [117][118][119][120][121][122][123] and chalcogen-bridged acenes, [124][125][126][127][128][129][130][131][132][133][134][135][136] but the transistor properties of these donors are still limited. [137][138][139][140][141][142][143][144] This section describes a new class o...…”

Section: Organic Conductors Based On Organic Semiconductorsmentioning

confidence: 99%

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Boundary research between organic conductors and transistors: new trends for functional molecular crystals

Kadoya

Higashino

2023

CrystEngComm

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Section: Organic Conductors Based On Organic Semiconductorsmentioning

confidence: 99%

Section: Organic Conductors Based On Organic Semiconductorsmentioning

confidence: 99%

Boundary research between organic conductors and transistors: new trends for functional molecular crystals

Kadoya

Higashino

2023

CrystEngComm

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“…In this context, sulfur-containing heterocycles, such as tetrathiafulvalenes (TTF) or thiophenes, which represent popular π-donating building blocks in organic semiconductors, play an important role in materials science. − However, sulfur-containing pyrene derivatives have only scarcely been reported to date. Examples include peri-condensed 1,6-dithiapyrene ( A ) − and tetrathionaphthalene ( C ), naphthodithiophenes E and F , − and phenanthro[4,5- bcd ]thiophene ( B ) , and phenaleno[1,9- bc ]thiophene ( D ) , (Scheme ). Compounds A and C are isoelectronic with pyrene in its oxidation state, while B , D , E, and F represent analogs of pyrene itself.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

Molenda,

Polkaehn,

Argüello Cordero

et al. 2023

J. Org. Chem.

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Thieno[2′,3′,4′:4,5]naphtho [1,8-cd]pyridines, S,N-doped pyrene analogs, were prepared by combination of Pd catalyzed cross-coupling reactions and acid-mediated cycloisomerization. The modular scope of the synthesis allowed for access to a variety of functionalized derivatives. The photophysical properties have been studied in detail by steady-state and femtosecond transient absorption accompanied by cyclic voltammetry and (TD)-DFT calculations. The introduction of a five-membered thiophene into the 2-azapyrene scaffold leads to redshifted emission and substantial effects on the excited state dynamics, e.g., quantum yield, lifetime, decay rates, and the ISC ability, which can be further tuned by the substitution pattern of the heterocyclic scaffold.

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“…During this process, the electric dipole moment of the microscopic particle will change to some extent, leading to varying the electrical or optical properties of the molecular material. CT is a common phenomenon in physical and chemical reactions. − Due to its rich dynamic behavior in the study of chemistry and physics, − charge-transfer plays an important role in many basic research and technical applications such as nanomanufacturing, , catalytic reaction, , and plasma-surface interaction . Back in the 1950s, Hagstrum opened up the CT research field by developing ion neutralization spectroscopy and made a key discussion of CT mechanisms and related kinetic processes .…”

Section: Introductionmentioning

confidence: 99%

Charge Transfer and Level Lifetime in Molecular Photon-Absorption upon the Quantum Impedance Lorentz Oscillator

et al. 2023

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On the strength of the new quantum impedance Lorentz oscillator (QILO) model, a charge-transfer method in molecular photon-absorption is proposed and imaged via the numerical simulations of 1- and 2-photon-absorption (1PA and 2PA) behaviors of the organic compounds LB3 and M4 in this paper. According to the frequencies at the peaks and the full width at half-maximums (FWHMs) of the linear absorptive spectra of the two compounds, we first calculate the effective quantum numbers before and after the electronic transitions. Thus, we obtain the molecular average dipole moments, i.e., 1.8728 × 10–29 C·m (5.6145 D) for LB3 and 1.9626 × 10–29 C·m (5.8838 D) for M4 in the ground state in the tetrahydrofuran (THF) solvent. Then, the molecular 2PA cross sections corresponding to wavelength are theoretically inferred and figured out by QILO. As a result, the theoretical cross sections turn out to be in good agreement with the experimental ones. Our results reveal such a charge-transfer image in 1PA near wavelength 425 nm, where an atomic electron of LB3 jumps from the ground-state ellipse orbit with the semimajor axis a i = 1.2492 × 10–10 m = 1.2492 Å and semiminor axis b i = 0.4363 Å to the excited-state circle (a j = b j = 2.5399 Å). In addition, during its 2PA process, the same transitional electron in the ground state is excited to the elliptic orbit with a j = 2.5399 Å and b j =1.3808 Å, in which the molecular dipole moment reaches as high as 3.4109 × 10–29 C·m (10.2256 D). In addition, we obtain a level-lifetime formula with the microparticle collision idea of thermal motion, which indicates that the level lifetime is proportional (not inverse) to the damping coefficient or FWHM of an absorptive spectrum. The lifetimes of the two compounds at some excited states are calculated and presented. This formula may be used as an experimental method to verify 1PA and 2PA transition selection rules. The QILO model exhibits the advantage of simplifying the calculation complexity and reducing the high cost associated with the first principle in dealing with quantum properties of optoelectronic materials.

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A new donor for charge-transfer systems: synthesis and properties of 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of (TMDTP)₃(PF₆)₂·2THF and TMDTP–TCNQ

Abstract: The heterocyclic donor molecule 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) has been synthesized in five steps. The charge-transfer complex, TMDTP–TCNQ, has been prepared and the salt, (TMDTP)3(PF6)2·2THF, obtained by electrocrystallization.

Cited by 3 publications

References 43 publications

Boundary research between organic conductors and transistors: new trends for functional molecular crystals

Boundary research between organic conductors and transistors: new trends for functional molecular crystals

Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

Charge Transfer and Level Lifetime in Molecular Photon-Absorption upon the Quantum Impedance Lorentz Oscillator

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