Co-crystals of polynuclear aromatic hydrocarbons and 9H-carbazole with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone acceptor: Varieties in crystal packing, Hirshfeld surface analysis and quantum-chemical studies

Fonarı, Marina S.; Rigin, Sergei; Lesse, Daniel; Timofeeva, Tatiana V.

doi:10.1016/j.molstruc.2023.134900

Cited by 3 publications

(3 citation statements)

References 57 publications

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“…Recently, single crystal X-ray diffraction spectroscopy was used to analyse the crystal structures of two anthracene-based co-crystals. [106] The 1 : 1 DA co-crystals of benz[a]anthracene and dibenz[a,c]anthracene with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), respectively assembled in mixed-stacks. However, due to varying extent of diverse π-π intermolecular interactions between donors and acceptor molecules, different crystal packings were observed in the two cases.…”

Section: -Acetyl-3-phenyl-5-(1-pyrenyl)pyrazoline (Appp) 1-(5-(anthra...mentioning

confidence: 99%

“…Recently, single crystal X‐ray diffraction spectroscopy was used to analyse the crystal structures of two anthracene‐based co‐crystals [106] . The 1 : 1 DA co‐crystals of benz[ a ]anthracene and dibenz[ a,c ]anthracene with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ), respectively assembled in mixed‐stacks.…”

Section: Polycyclic Aromatic Hydrocarbons As Donorsmentioning

confidence: 99%

“…The thermodynamic parameters were calculated by van't Hoff equations and were found to be spontaneous and exothermic. Recently, a co‐crystal of 9H‐carbazole with DDQ was prepared, and its crystal structure was determined using single‐crystal X‐ray diffraction analysis [106] . It was found to have a high crystal density with herringbone‐type crystal packing involving rearranged intermolecular interactions.…”

Section: Nitrogen Heterocycles As Donorsmentioning

confidence: 99%

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Organic Donor‐Acceptor Complexes As Potential Semiconducting Materials

Mathur,

Gupta,

Bansal

2024

Chemistry A European J

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In this review article, the synthesis, characterization and physico‐chemical properties of the organic donor‐acceptor complexes are highlighted and a special emphasis has been placed on developing them as semiconducting materials. The electron‐rich molecules, i.e., donors have been broadly grouped in three categories, namely polycyclic aromatic hydrocarbons, nitrogen heterocycles and sulphur containing aromatic donors. The reactions of these classes of the donors with the acceptors, namely tetracyanoquinodimethane (TCNQ), tetracyanoethylene (TCNE), tetracyanobenzene (TCNB), benzoquinone, pyromellitic dianhydride and pyromellitic diimides, fullerenes, phenazine, benzothiadiazole, naphthalimide, DMAD, maleic anhydride, viologens and naphthalene diimide are described. The potential applications of the resulting DA complexes for physico‐electronic purposes are also included. The theoretical investigation of many of these products with a view to rationalise their observed physico‐chemical properties is also discussed.

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Section: -Acetyl-3-phenyl-5-(1-pyrenyl)pyrazoline (Appp) 1-(5-(anthra...mentioning

confidence: 99%

Section: Polycyclic Aromatic Hydrocarbons As Donorsmentioning

confidence: 99%

Section: Nitrogen Heterocycles As Donorsmentioning

confidence: 99%

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Organic Donor‐Acceptor Complexes As Potential Semiconducting Materials

Mathur,

Gupta,

Bansal

2024

Chemistry A European J

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Frustrated Radical Pairs: From Fleeting Intermediates to Isolable Species

van der Zee,

Hofman,

Mathew

et al. 2024

Chemistry A European J

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We present the design and comprehensive investigation of stable para‐substituted triarylamine–2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) radical ion pairs (RIPs) generated via single‐electron transfer (SET). We quantified the degree of SET in both solution and solid phases, utilising a suite of spectroscopic techniques including IR, EPR, NMR, and single‐crystal X‐ray diffraction (SC–XRD). Our findings reveal that the extent of SET is significantly influenced by the nature of the substituents (MeO > tBu > Br) and the polarity of the solvent (MeCN > DCM > toluene). The radical ion pair [(pMeOPh)3N]•+[DDQ]•– was unambiguously identified using EPR and UV–vis spectroscopy, and its structure was confirmed by SC–XRD. Detailed analysis indicates an open‐shell singlet ground state with a thermally accessible triplet state, as corroborated by EPR, magnetic susceptibility measurements, and DFT calculations. This study offers crucial insights into the mechanistic pathways of RIP formation and tuning both in solution and solid states, laying the groundwork for future exploration of their reactivity and potential applications.

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DTT-DDQ Mixed-Stack Organic Charge-Transfer Crystals with Near-Infrared Absorption

Friday,

Kelley,

Perez

et al. 2024

Crystal Growth & Design

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Dithieno[3,thiophene (DTT) is a common molecular motif in organic electronics. We find that it forms a 1:1 charge-transfer complex (CTC) with the electron acceptor 2,3dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The 1:1 complex has an alternating donor/acceptor mixed-stack structure, and an intense near-infrared absorption band. Vibrational spectroscopy and electronic structure calculations are used to further understand the partial ionization induced by the DTT/DDQ complex.

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Co-crystals of polynuclear aromatic hydrocarbons and 9H-carbazole with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone acceptor: Varieties in crystal packing, Hirshfeld surface analysis and quantum-chemical studies

Cited by 3 publications

References 57 publications

Organic Donor‐Acceptor Complexes As Potential Semiconducting Materials

Organic Donor‐Acceptor Complexes As Potential Semiconducting Materials

Frustrated Radical Pairs: From Fleeting Intermediates to Isolable Species

DTT-DDQ Mixed-Stack Organic Charge-Transfer Crystals with Near-Infrared Absorption

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