Effect of N-methyl and ethyl on phosphorescence of carbazole in cocrystals assembled by C-I⋯π halogen bond, π-hole⋯π bond and other interactions using 1,4-diiodotetrafluorobenzene as donor

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 289, Issue , 2014, Pages 31-38

  Zhu, Qing ^a   Gao, Yuan Jun ^a   Gao, Hai Yue ^a   Jin, Wei Jun ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

CI halogen bond; Modulated phosphorescence; Steric effect; hole bond

Indexed keywords

EID: 84902657325     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2014.05.010     Document Type: Article

References (35)

1. A. Köhler, J.S. Wilson, and R.H. Friend Fluorescence and phosphorescence in organic materials Adv. Mater. 14 2002 701 707
2. M. Muccini A bright future for organic field-effect transistors Nat. Mater. 5 2006 605 613 (Pubitemid 44157676)
3. M. Banerjee, V.S. Vyas, S.V. Lindeman, and R. Rathore Isolation and X-ray structural characterization of tetraisopropylpyrene cation radical Chem. Commun. 2008 1889 1891 (Pubitemid 351503466)
4. P. Metrangolo, H. Neukirch, T. Pilati, and G. Resnati Halogen bonding based recognition processes: a world parallel to hydrogen bonding Acc. Chem. Res. 38 2005 386 395 (Pubitemid 40816650)
5. P. Metrangolo, J.S. Murray, T. Pilati, P. Politzer, G. Resnati, and G. Terraneo The fluorine atom as a halogen bond donor, viz. a positive site CrystEngComm 13 2011 6593 6596
6. G.R. Desiraju, P. Shing Ho, L. Kloo, A.C. Legon, R. Marquardt, P. Metrangolo, P. Politzer, G. Resnati, and K. Rissanen Definition of the halogen bond Pure Appl. Chem. 85 2013 1711 1713
7. R. Liantonio, P. Metrangolo, T. Pilati, and G. Resnati 4,4′-Bipyridine 1,2-diiodo-3,4,5,6-tetrafluorobenzene Acta Crystallogr. Sect. E 58 2002 o575-o577
8. J.-L. Syssa-Magale, K. Boubekeur, P. Palvadeau, A. Meerschaut, and B. Schollhorn The tailoring of crystal structures via the self-assembly of organic coordination compounds by N⋯I non-covalent halogen bonds: co-crystals of sterically hindered N-heterocycles and 1,4-diiodotetrafluorobenzene CrystEngComm 7 2005 302 308 (Pubitemid 40727401)
9. J.-L. Syssa-Magale, K. Boubekeur, and B. Schollhorn First molecular self-assembly of 1,4-diiodotetrafluorobenzene and a ketone via (O⋯I) non-covalent halogen bonds J. Mol. Struct. 737 2005 103 107 (Pubitemid 40173955)
10. L. Russo, S. Biella, M. Lahtinen, R. Liantonio, P. Metrangolo, G. Resnati, and K. Rissanen Solution stoichiometry determines crystal stoichiometry in halogen-bonded supramolecular complexes CrystEngComm 9 2007 341 344
11. D. Cinčić, T. Friščić, and W. Jones Experimental and database studies of three-centered halogen bonds with bifurcated acceptors present in molecular crystals, cocrystals and salts CrystEngComm 13 2011 3224 3231
12. T. Clark, M. Hennemann, J.S. Murray, and P. Politzer Halogen bonding: the σ-hole J. Mol. Model. 13 2007 291 296
13. J.S. Murray, P. Lane, T. Clark, K.E. Riley, and P. Politzer σ-Holes, π-holes and electrostatically-driven interactions J. Mol. Model. 18 2012 541 548
14. P. Politzer, J.S. Murray, and T. Clark Halogen bonding: an electrostatically-driven highly directional noncovalent interaction Phys. Chem. Chem. Phys. 12 2010 7748 7757
15. P. Politzer, J.S. Murray, and M.C. Concha σ-hole bonding between like atoms; a fallacy of atomic charges J. Mol. Model. 14 2008 659 665
16. J.S. Murray, P. Lane, and P. Politzer A predicted new type of directional noncovalent interaction Int. J. Quantum Chem. 107 2007 2286 2292 (Pubitemid 47265393)
17. P. Politzer, and J.S. Murray Halogen bonding, an interim discussion ChemPhysChem 14 2013 278 294
18. A. Frontera, P. Gamez, M. Mascal, T.J. Mooibroek, and J. Reedijk Putting anion-π interactions into perspective Angew. Chem. Int. Ed. 50 2011 9564 9583
19. 5X (X = F, Cl, Br, I) and the chloride anion and its potential application in separation science J. Phys. Chem. B 118 2014 1080 1087
20. 5X (X = F, Cl, Br, I) and triethylphosphine oxide J. Mol. Model. 19 2013 5007 5014
21. X. Pang, H. Wang, X.R. Zhao, and W.J. Jin Co-crystallization turned on the phosphorescence of phenanthrene by CBr⋯π halogen bonding, π-hole⋯π bonding and other assisting interactions CrystEngComm 15 2013 2722 2730
22. Q.J. Shen, H.Q. Wei, W.S. Zou, H.L. Sun, and W.J. Jin Cocrystals assembled by pyrene and 1,2- or 1,4-diiodotetrafluorobenzenes and their phosphorescing behaviors modulated by local molecular environment CrystEngComm 14 2012 1010 1015
23. H.Y. Gao, Q.J. Shen, X.R. Zhao, X.Q. Yan, X. Pang, and W.J. Jin Phosphorescent co-crystal assembled by 1,4-diiodotetrafluorobenzene with carbazole based on CI⋯π halogen bond J. Mater. Chem. 22 2012 5336 5343
24. H.Y. Gao, X.R. Zhao, H. Wang, X. Pang, and W.J. Jin Phosphorescent cocrystals assembled by 1,4-diiodotetrafluorobenzene and fluorene and its heterocyclic analogues based on CI⋯π halogen bond Crystal Growth Des. 12 2012 4377 4387
25. Q.J. Shen, X. Pang, X.R. Zhao, H.Y. Gao, H.L. Sun, and W.J. Jin Phosphorescent cocrystals constructed by 1,4-diiodotetrafluorobenzene and polyaromatic hydrocarbons based on CI⋯π halogen bond and other assisting weak interactions CrystEngComm 14 2012 5027 5034
26. G.M. Sheldrick SHELXTL Version 5.1 1998 Bruker Analytical X-ray Instruments Inc. Madison, Wisconsin, USA
27. G.M. Sheldrick SHELX-97, PC Version 1997 University of Göttingen Germany
28. Q. Zhu, H. Wang, X.R. Zhao, and W.J. Jin The phosphorescent behaviors of 9-bromo- and 9-iodophenanthrene in crystals modulated by π-π interactions, CH⋯π hydrogen bond and CI⋯π halogen bond J. Photochem. Photobiol. A 274 2014 98 107
29. P. Politzer, and J.S. Murray The fundamental nature and role of the electrostatic potential in atoms and molecules Theor. Chem. Acc. 108 2002 134 142 (Pubitemid 36160437)
30. T.M. Figueira-Duarte, and K. Müllen Pyrene-based materials for organic electronics Chem. Rev. 111 2011 7260 7314
31. W.J. Liang, Y. Wang, F. Feng, and W.J. Jin Novel self-protective phosphorescence from crystalline nanoparticles assembled by 3-bromo- and 3-iodo-carbazoles based on halogen-halogen interaction in suspension solutions Anal. Chim. Acta 572 2006 295 302
32. P. Cardillo, E. Corradi, A. Lunghi, S.V. Meille, T.M. Messina, P. Metrangolo, and G. Resnati The N⋯I intermolecular interaction as a general protocol for the formation of perfluorocarbon-hydrocarbon supramolecular architectures Tetrahedron 56 2000 5535 5550 (Pubitemid 30637440)
33. R. Liantonio, S. Luzzati, P. Metrangolo, T. Pilati, and G. Resnati Perfluorocarbon-hydrocarbon self-assembly. Part 16: Anilines as new electron donor modules for halogen bonded infinite chain formation Tetrahedron 58 2002 4023 4029 (Pubitemid 34465672)
34. M.T. Messina, P. Metrangolo, W. Panzeri, T. Pilati, and G. Resnati Intermolecular recognition between hydrocarbon oxygen-donors and perfluorocarbon iodine-acceptors: the shortest O⋯I non-covalent bond Tetrahedron 57 2001 8543 8550 (Pubitemid 32905521)
35. G.R. Hanson, P. Jensen, J. McMurtrie, L. Rintoul, and A.S. Micallef Halogen bonding between an isoindoline nitroxide and 1,4- diiodotetrafluorobenzene: new tools and tectons for self-assembling organic spin systems Chem. A: Eur. J. 15 2009 4156 4164