Study of charge transfer interaction modes in the mixed Donor-Acceptor cocrystals of pyrene derivatives and TCNQ: A combined structural, thermal, spectroscopic, and hirshfeld surfaces analysis

Journal of Solid State Chemistry - Tập 266 - Trang 112-120 - 2018
Rabia Usman1, Arshad Khan2, Hao Sun1, Mingliang Wang1
1School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, PR China
2State Key Laboratory of Bioelectronics, Southeast University, Nanjing 210096, PR China

Tài liệu tham khảo

Averkiev, 2018, Evidence of low-temperature phase transition in Tetracene–Tetracyanoquinodimethane Complex, Cryst. Growth Des., 10.1021/acs.cgd.8b00501 Qin, 2014, Charge‐transfer complex crystal based on extended‐π‐conjugated acceptor and sulfur‐bridged Annulene: charge‐transfer interaction and remarkable high ambipolar transport characteristics, Adv. Mater., 26, 4093, 10.1002/adma.201400056 Sun, 1996, Electronic switching properties in nanometer-sized Cu-(TCNQ)2 powder compactions, Solid State Commun., 99, 237, 10.1016/0038-1098(96)00252-9 Sun, 1997, Crystal structure of bis(tetraethylammonium) bis[4,5-disulfanyl-1,3-dithiol-2-onato(2-)]nickelate(II) and spectroscopic and electrical properties of related oxidized complexes, J. Chem. Soc., Dalton Trans., 2, 277, 10.1039/a604434d Goetz, 2014, Charge-transfer complexes: new perspectives on an old class of compounds, J. Mater. Chem. C., 2, 3065, 10.1039/C3TC32062F Sagade, 2013, A charge transfer single crystal field effect transistor operating at low voltages, Chem. Commun., 49, 5847, 10.1039/c3cc41841c Yoshida, 2014, Isotropic three-dimensional molecular conductor based on the coronene radical cation, Eur. J. Inorg. Chem., 2014, 3871, 10.1002/ejic.201400119 Li, 2014, Self-assembly of intramolecular charge-transfer compounds into functional molecular systems, Acc. Chem. Res, 47, 1186, 10.1021/ar400264e Fourmigué, 2004, Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors, Chem. Rev., 104, 5379, 10.1021/cr030645s Tayi, 2012, Room-temperature ferroelectricity in supramolecular networks of charge-transfer complexes, Nature, 488, 485, 10.1038/nature11395 Odom, 2010, Microencapsulation: restoration of conductivity with TTF-TCNQ Charge-Transfer Salts Adv. Funct. Mater 11/2010), Adv. Funct. Mater., 20, 1721, 10.1002/adfm.201000159 Singleton, 2002, Why do physicists love charge-transfer salts?, J. Solid State Chem., 168, 675, 10.1006/jssc.2002.9766 Allemand, 1991, Organic Molecular Soft Ferromagnetism in a Fullerene, 253, 301 Enoki, 2004, Magnetic TTF-based charge-transfer complexes, Chem. Rev., 104, 5449, 10.1021/cr0306438 Kang, 2012, Complex in small-molecule solar cells based on contorted aromatic molecules, Angew. Chem. Int. Ed., 51, 8594, 10.1002/anie.201203330 Singleton, 2002, Quasi-two-dimensional organic superconductors: a review, Contemp. Phys., 43, 63, 10.1080/00107510110108681 Kondo, 1998, Spin fluctuation-induced superconductivity in organic compounds, J. Phys. Soc. Jpn, 67, 3695, 10.1143/JPSJ.67.3695 Khan, 2016, Organic charge-transfer complexes for the selective accommodation of aromatic isomers using anthracene derivatives and TCNQ, New J. Chem., 40, 5277, 10.1039/C5NJ03442F Khan, 2017, Molecular marriage via charge transfer interaction in organic charge transfer Co-crystals toward solid-state fluorescence modulation, Cryst. Growth Des., 17, 1251, 10.1021/acs.cgd.6b01636 Sun, 2015, Understanding charge-transfer interaction mode in cocrystals and solvates of 1-Phenyl-3-(pyren-1-yl) Prop-2-en-1-one and TCNQ, Cryst. Growth Des., 15, 4032, 10.1021/acs.cgd.5b00656 Feng, 2013, Tuning solid-state fluorescence of pyrene derivatives via a cocrystal strategy, CrystEngComm, 15, 3623, 10.1039/c3ce27102a An, 2015, Facile preparation of α-Cyano-α,ω-Diaryloligovinylenes: a new class of color-tunable solid emitters, Chem. Asian J., 10, 1959, 10.1002/asia.201500473 Sheldrick, 2015, Crystal structure refinement with SHELXL, Acta Crystallogr., Sect. C., 71, 3, 10.1107/S2053229614024218 Chappell, 1981, Degree of charge transfer in organic conductors by infrared absorption spectroscopy, J. Am. Chem. Soc., 103, 2442, 10.1021/ja00399a066 Achary, 2016, Unprecedented charge-transfer complex of fused diporphyrin as near-infrared absorption-induced high-aspect-ratio nanorods, Chem. Asian J., 11, 3498, 10.1002/asia.201601363 Yu, 2013, A photoconductive charge-transfer crystal with mixed-stacking donor-acceptor heterojunctions within the lattice, Chem. Commun., 49, 54, 10.1039/C2CC37655E Peng, 2016, Crystal growth, homo–LUMO engineering, and charge transfer degree in Perylene-FxTCNQ (x = 1, 2, 4) organic charge transfer binary compounds, Cryst. Growth Des., 16, 3019, 10.1021/acs.cgd.5b01675 Morherr, 2016, Crystal growth of new charge-transfer salts based on π-conjugated donor molecules, Phys. B, 496, 98, 10.1016/j.physb.2016.05.023 Dobrowolski, 2014, Structural diversities of charge transfer organic complexes. focus on benzenoid hydrocarbons and 7,7,8,8-tetracyanoquinodimethane, CrystEngComm, 16, 415, 10.1039/C3CE41703D Vermeulen, 2014, Charge transport properties of perylene–TCNQ crystals: the effect of stoichiometry, J. Phys. Chem. C., 118, 24688, 10.1021/jp508520x Qin, 2017, Structure and characterization of charge transfer complexes of benzo[1,2-b:3,4-b′:5,6-b′′]trithiophene [C3h-BTT], CrystEngComm, 19, 6355, 10.1039/C7CE01471F Spackman, 2009, Hirshfeld surface analysis, CrystEngComm, 11, 19, 10.1039/B818330A Spackman, 2002, Fingerprinting intermolecular interactions in molecular crystals, CrystEngComm, 4, 378, 10.1039/B203191B Goud, 2017, Impact of hydrogen and halogen bonding interactions on the packing and ionicity of charge-transfer cocrystals, Cryst. Growth Des., 17, 328, 10.1021/acs.cgd.6b01548