TY  - JOUR
A1  - Hoffmann, Katrin
A1  - Dietzel, Birgit
A1  - Schulz, Burkhard
A1  - Reck, Guenter
A1  - Hoffmann, Angelika
A1  - Orgzall, Ingo
A1  - Resch-Genger, Ute
A1  - Emmerling, Franziska
T1  - Combined structural and fluorescence studies of methyl-substituted 2,5-diphenyl-1,3,4-oxadiazoles - Relation between electronic properties and packing motifs
JF  - Journal of molecular structure
N2  - Prerequisite for the rational design of functional organic materials with tailor-made electronic properties is the knowledge of the structure-property relationship for the specific class of molecules under consideration. This encouraged us to systematically study the influence of the molecular structure and substitution pattern of aromatically substituted 1,3,4-oxadiazoles on the electronic properties and packing motifs of these molecules and on the interplay of these factors. For this purpose, seven diphenyl-oxadiazoles equipped with methyl substituents in the ortho- and meta-position(s) were synthesized and characterized. Absorption and fluorescence spectra in solution served here as tools to monitor substitution-induced changes in the electronic properties of the individual molecules whereas X-ray and optical measurements in the solid state provided information on the interplay of electronic and packing effects. In solution, the spectral position of the absorption maximum, the size of Stokes shift, and the fluorescence quantum yield are considerably affected by ortho-substitution in three or four ortho-positions. This results in blue shifted absorption bands, increased Stokes shifts, and reduced fluorescence quantum yields whereas the spectral position and vibrational structure of the emission bands remain more or less unaffected. In the crystalline state, however, the spectral position and shape of the emission bands display a strong dependence on the molecular structure and/or packing motifs that seem to control the amount of dye-dye-interactions. These observations reveal the limited value of commonly reported absorption and fluorescence measurements in solution for a straightforward comparison of spectroscopic results with single X-ray crystallography. This underlines the importance of solid state spectroscopic studies for a better understanding of the interplay of electronic effects and molecular order.
KW  - Diphenyl-oxadiazoles
KW  - X-ray structure
KW  - Packing motif
KW  - Optical properties
KW  - Fluorescence quantum yield
Y1  - 2011
U6  - https://doi.org/10.1016/j.molstruc.2010.11.071
SN  - 0022-2860
VL  - 988
IS  - 1-3
SP  - 35
EP  - 46
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - GEN
A1  - Abramowski, Attila
A1  - Aharonian, Felix A.
A1  - Benkhali, Faical Ait
A1  - Akhperjanian, A. G.
A1  - Angüner, Ekrem Oǧuzhan
A1  - Backes, Michael
A1  - Balenderan, Shangkari
A1  - Balzer, Arnim
A1  - Barnacka, Anna
A1  - Becherini, Yvonne
A1  - Tjus, Julia Becker
A1  - Berge, David
A1  - Bernhard, Sabrina
A1  - Bernlöhr, Konrad
A1  - Birsin, E.
A1  - Biteau, Jonathan
A1  - Böttcher, Markus
A1  - Boisson, Catherine
A1  - Bolmont, J.
A1  - Bordas, Pol
A1  - Bregeon, Johan
A1  - Brun, Francois
A1  - Brun, Pierre
A1  - Bryan, Mark
A1  - Bulik, Tomasz
A1  - Carrigan, Svenja
A1  - Casanova, Sabrina
A1  - Chadwick, Paula M.
A1  - Chakraborty, Nachiketa
A1  - Chalme-Calvet, R.
A1  - Chaves, Ryan C. G.
A1  - Chretien, M.
A1  - Colafrancesco, Sergio
A1  - Cologna, Gabriele
A1  - Conrad, Jan
A1  - Couturier, Claire
A1  - Cui, Yudong
A1  - Davids, Isak Delberth
A1  - Degrange, Bernhard
A1  - Deil, Christoph
A1  - deWilt, P.
A1  - Djannati-Ataï, A.
A1  - Domainko, Wilfried
A1  - Donath, Axel
A1  - Dubus, G.
A1  - Dutson, K.
A1  - Dyks, J.
A1  - Dyrda, M.
A1  - Edwards, Tanya
A1  - Egberts, Kathrin
A1  - Eger, Peter
A1  - Espigat, P.
A1  - Farnier, C.
A1  - Fegan, Stephen
A1  - Feinstein, Fabrice
A1  - Fernandes, Milton Virgilio
A1  - Fernandez, Diane
A1  - Fiasson, A.
A1  - Fontaine, Gerard
A1  - Förster, Andreas
A1  - Fuessling, M.
A1  - Gabici, S.
A1  - Gajdus, M.
A1  - Gallant, Yves A.
A1  - Garrigoux, Tania
A1  - Giavitto, G.
A1  - Giebels, Berrie
A1  - Glicenstein, Jean-Francois
A1  - Gottschall, Daniel
A1  - Grondin, M. -H.
A1  - Grudzinska, M.
A1  - Hadasch, Daniela
A1  - Haeffner, S.
A1  - Hahn, Joachim
A1  - Harris, Jonathan
A1  - Heinzelmann, Götz
A1  - Henri, G.
A1  - Hermann, German
A1  - Hervet, O.
A1  - Hillert, Andreas
A1  - Hinton, James Anthony
A1  - Hofmann, Werner
A1  - Hofverberg, Petter
A1  - Holler, Markus
A1  - Horns, Dieter
A1  - Ivascenko, Alex
A1  - Jacholkowska, A.
A1  - Jahn, C.
A1  - Jamrozy, Marek
A1  - Janiak, M.
A1  - Jankowsky, F.
A1  - Jung-Richardt, I.
A1  - Kastendieck, Max Anton
A1  - Katarzynski, K.
A1  - Katz, U.
A1  - Kaufmann, S.
A1  - Khelifi, B.
A1  - Kieffer, Michel
A1  - Klepser, S.
A1  - Klochkov, Dmitry
A1  - Kluzniak, W.
A1  - Kolitzus, David
A1  - Komin, Nu
A1  - Kosack, Karl
A1  - Krakau, Steffen
A1  - Krayzel, F.
A1  - Krueger, Pat P.
A1  - Laffon, H.
A1  - Lamanna, G.
A1  - Lefaucheur, J.
A1  - Lefranc, Valentin
A1  - Lemiere, A.
A1  - Lemoine-Goumard, M.
A1  - Lenain, J. -P.
A1  - Lohse, Thomas
A1  - Lopatin, A.
A1  - Lu, Chia-Chun
A1  - Marandon, Vincent
A1  - Marcowith, Alexandre
A1  - Marx, Ramin
A1  - Maurin, G.
A1  - Maxted, Nigel
A1  - Mayer, Michael
A1  - McComb, T. J. Lowry
A1  - Mehault, J.
A1  - Meintjes, P. J.
A1  - Menzler, Ulf
A1  - Meyer, M.
A1  - Mitchell, Alison M. W.
A1  - Moderski, R.
A1  - Mohamed, M.
A1  - Mora, K.
A1  - Moulin, Emmanuel
A1  - Murach, Thomas
A1  - de Naurois, Mathieu
A1  - Niemiec, J.
A1  - Nolan, Sam J.
A1  - Oakes, Louise
A1  - Odaka, Hirokazu
A1  - Ohm, S.
A1  - Optiz, Björn
A1  - Ostrowski, Michal
A1  - Oya, I.
A1  - Panter, Michael
A1  - Parsons, R. Daniel
A1  - Arribas, M. Paz
A1  - Pekeur, Nikki W.
A1  - Pelletier, G.
A1  - Petrucci, P. -O.
A1  - Peyaud, B.
A1  - Pita, S.
A1  - Poon, Helen
A1  - Pühlhofer, Gerd
A1  - Punch, M.
A1  - Quirrenbach, A.
A1  - Raab, S.
A1  - Reichardt, I.
A1  - Reimer, Anita
A1  - Reimer, Olaf
A1  - Renaud, Metz
A1  - de los Reyes, Raquel
A1  - Rieger, Frank
A1  - Romoli, C.
A1  - Rosier-Lees, S.
A1  - Rowell, G.
A1  - Rudak, B.
A1  - Rulten, C. B.
A1  - Sahakian, Vardan
A1  - Salek, D.
A1  - Sanchez, David M.
A1  - Santangelo, Andrea
A1  - Schlickeiser, Reinhard
A1  - Schuessler, F.
A1  - Schulz, A.
A1  - Schwanke, Ullrich
A1  - Schwarzburg, S.
A1  - Schwemmer, S.
A1  - Sol, H.
A1  - Spanier, Felix
A1  - Spengler, G.
A1  - Spies, Franziska
A1  - Stawarz, Lukasz
A1  - Steenkamp, Riaan
A1  - Stegmann, Christian
A1  - Stinzing, F.
A1  - Stycz, K.
A1  - Sushch, Iurii
A1  - Tavernet, J. -P.
A1  - Tavernier, T.
A1  - Taylor, A. M.
A1  - Terrier, R.
A1  - Tluczykont, Martin
A1  - Trichard, C.
A1  - Valerius, K.
A1  - van Eldik, C.
A1  - van Soelen, B.
A1  - Vasileiadis, Georges
A1  - Veh, J.
A1  - Venter, Christo
A1  - Viana, Aion
A1  - Vincent, P.
A1  - Vink, Jacco
A1  - Völk, Heinrich J.
A1  - Volpe, Francesca
A1  - Vorster, Martine
A1  - Vuillaume, T.
A1  - Wagner, S. J.
A1  - Wagner, P.
A1  - Wagner, R. M.
A1  - Ward, Martin
A1  - Weidinger, Matthias
A1  - Weitzel, Quirin
A1  - White, R.
A1  - Wierzcholska, A.
A1  - Willmann, P.
A1  - Woernlein, A.
A1  - Wouters, D.
A1  - Yang, Ruizhi
A1  - Zabalza, Victor
A1  - Zaborov, Dmitry
A1  - Zacharias, M.
A1  - Zdziarski, A. A.
A1  - Zech, Alraune
A1  - Zechlin, Hannes -S.
T1  - H.E.S.S. detection of TeV emission from the interaction region between the supernova remnant G349.7+0.2 and a molecular cloud (vol 574, A100, 2015)
T2  - Astronomy and astrophysics : an international weekly journal
KW  - gamma rays: general
KW  - ISM: supernova remnants
KW  - ISM: clouds
KW  - errata, addenda
Y1  - 2015
U6  - https://doi.org/10.1051/0004-6361/201425070e
SN  - 1432-0746
VL  - 580
PB  - EDP Sciences
CY  - Les Ulis
ER  - 
TY  - JOUR
A1  - Emmerling, Franziska
A1  - Orgzall, Ingo
A1  - Dietzel, Birgit
A1  - Schulz, Burkhard
A1  - Larrucea, Julen
T1  - Ordering the amorphous - Structures in PBD LED materials
JF  - Journal of molecular structure
N2  - The class of 2,5 disubstituted-1,3,4-oxadiazoles containing a biphenyl unit on one side is intensively used as electron transport materials to enhance the performance of organic light emitting diodes (OLEDs). In contrast to the ongoing research on these materials insights in their structure-property relationships are still incomplete. To overcome the structural tentativeness and ambiguities the crystal structures of 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole, that of the related compound 2-(4-biphenylyl)-5-phenyl-1,3,4-oxadiazole and of 2-(4-biphenylyl)-5-(2,6-dimethylphenyl)-1,3,4-oxadiazole are determined. A comparison with the results of GAUSSIAN03 calculations and similar compounds in the Cambridge Structural Database leads to a profound characterization.
KW  - OLED
KW  - PBD
KW  - Diphenyl-1,3,4-oxadiazole
KW  - Crystallization
Y1  - 2012
U6  - https://doi.org/10.1016/j.molstruc.2012.04.040
SN  - 0022-2860
VL  - 1030
IS  - 23
SP  - 209
EP  - 215
PB  - Elsevier
CY  - Amsterdam
ER  - 
TY  - JOUR
A1  - Emmerling, Franziska
A1  - Orgzall, Ingo
A1  - Reck, Günter
A1  - Schulz, Burkhard W.
A1  - Stockhause, Sabine
A1  - Schulz, Burkhard
T1  - Structures of substituted di-aryl-1, 3,4-oxadiazole derivatives: 2,5-bis(pyridyl)- and 2,5-bis(aminophenyl)-substitution
JF  - Journal of molecular structure
N2  - Crystal structures of four different di-aryl-1,3,4-oxadiazole compounds (aryl = 2-pyridyl-, 3-pyridyl-, 2-aminophenyl-, 3-aminophenyl-) are determined. Crystallization of di(2-pyridyl)-1,3,4-oxadiazole yielded monoclinic and triclinic polymorphs. The structures are characterized by the occurrence of pi-pi interactions. Additionally, in case of the aminophenyl compounds intra- as well as intermolecular hydrogen bonds are found that influence the packing motif as well. Since these molecules are often used as ligands in metal-organic complexes similarities and differences of the molecular conformation between the molecules in the pure crystals and that of the ligands in the complexes are discussed. (c) 2006 Elsevier B.V. All rights reserved.
KW  - crystal structure
KW  - 1,3,4-oxadiazole
KW  - molecular conformation
KW  - hydrogen bonds
Y1  - 2006
U6  - https://doi.org/10.1016/j.molstruc.2006.03.076
SN  - 0022-2860
VL  - 800
IS  - 1-3
SP  - 74
EP  - 84
PB  - Elsevier
CY  - Amsterdam
ER  -