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Diindeno[1,2-b:2',1'-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties.

ABSTRACT: Diindeno[1,2-b:2',1'-n]perylene, a new derivative of the indenoacene family was synthesized, and its electronic, electrochemical, and electrical properties were investigated. This material has a closed shell electronic configuration which corresponds to a quinoidal structure with a low band gap of 1.35 eV. Molecular packing in the single crystal was studied by single-crystal X-ray structural analysis, and this information was subsequently used in the determination of the charge transfer integrals via density functional theory methods. The charge-carrier transport properties of the diindeno[1,2-b:2',1'-n]perylene-5,12-dione and diindeno[1,2-b:2',1'-n]perylene derivatives were investigated through the fabrication and characterization of field-effect transistors via both vacuum-deposited and solution-processed films, respectively. Diindeno[1,2-b:2',1'-n]perylene exhibited a field-effect behaviour with a hole mobility up to 1.7 × 10-3 cm2 V-1 s-1 when the active layer was solution-processed.

SUBMITTER: Sbargoud K

PROVIDER: S-EPMC5659070 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Diindeno[1,2-b:2',1'-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties.

Sbargoud Kamal K Mamada Masashi M Marrot Jérôme J Tokito Shizuo S Yassar Abderrahim A Frigoli Michel M

Chemical science 20150326 6

Diindeno[1,2-b:2',1'-n]perylene, a new derivative of the indenoacene family was synthesized, and its electronic, electrochemical, and electrical properties were investigated. This material has a closed shell electronic configuration which corresponds to a quinoidal structure with a low band gap of 1.35 eV. Molecular packing in the single crystal was studied by single-crystal X-ray structural analysis, and this information was subsequently used in the determination of the charge tra ...[more]

PMID: 29511505

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Project description:A series of oligothiophene bis(dioxolene) complexes, SQ-Thn-SQ (SQ = S = ½TpCum,MeZnII(3-tert-butyl-orthosemiquinonate); TpCum,Me = tris(5-cumenyl-3-methylpyrazolyl)borate anion) have been synthesized, structurally characterized, and studied as a function of the number of thiophene bridging units, n (n = 0-3) using a combination of variable-temperature (VT) electronic absorption and EPR spectroscopies, and VT magnetic susceptibility measurements. The thiophene bridge bond lengths determined by X-ray crystallography display dramatic differences across the SQ-Thn-SQ series. Bridge bond deviation values (Σ|Δi|) display a progressive change in the nature of the bridge fragment bonding as the number of thiophene groups increases, with quinoidal bridge character for n = 1 (SQ-Th-SQ) and biradical character with "aromatic" bridge bond lengths for n = 3 (SQ-Th3-SQ). Remarkably, for n = 2 (SQ-Th2-SQ) the nature of the bridge fragment is intermediate between quinoid and biradical aromatic, which we describe as having open-shell character as opposed to biradicaloid since the open-shell biradical configuration does not have the correct symmetry to mix with the quinoidal ground-state configuration. This bridge bonding character is reflected in the energies of the lowest lying open-shell states for these three molecules. The SQ-Th-SQ molecule is diamagnetic at all temperatures studied, and we provide evidence for SQ-SQ antiferromagnetic exchange coupling and population of triplet states in SQ-Th2-SQ and SQ-Th3-SQ, with JSQ-SQ(ave) = -279 cm-1 (VT EPR/electronic absorption/magnetic susceptibility) and JSQ-SQ = -117 cm-1 (VT EPR/electronic absorption/magnetic susceptibility), respectively. The results have been interpreted in the context of state configurational mixing within a simplified 4-electron, 3-orbital model that explicitly contains contributions of a bridge fragment. Variable-temperature spectroscopic- and magnetic susceptibility data are consistent with two low-lying open-shell states for SQ-Th3-SQ, but three low-lying states (one closed-shell and two open-shell) for SQ-Th2-SQ. This model provides a simple symmetry-based framework to understand the continuum of electronic and geometric structures of this class of molecules as a function of the number of thiophene units in the bridge.

Dataset Information

Diindeno[1,2-b:2',1'-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties.

Publications

Diindeno[1,2-<i>b</i>:2',1'-<i>n</i>]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties.

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