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Powder X‐ray diffraction as a powerful tool to exploit in organic electronics: shedding light on the first N , N ′, N ′′‐trialkyldiindolocarbazole
Author(s) -
Vilche Anna,
Bujaldón Roger,
Alcobé Xavier,
Velasco Dolores,
Puigjaner Cristina
Publication year - 2022
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520622001858
Subject(s) - crystallography , powder diffraction , stacking , organic electronics , crystal (programming language) , organic semiconductor , materials science , crystal structure , molecule , diffraction , carbazole , intermolecular force , chemistry , transistor , optoelectronics , physics , optics , computer science , organic chemistry , quantum mechanics , voltage , programming language
The first crystal structure of a fully N ‐alkylated diindolocarbazole derivative, namely, 5,8,14‐tributyldiindolo[3,2‐ b ;2′,3′‐ h ]carbazole ( 1 , C 36 H 39 N 3 ), has been determined from laboratory powder X‐ray diffraction (PXRD) data. A complex trigonal structure with a high‐volume unit cell of 12987 Å 3 was found, with a very long a (= b ) [52.8790 (14) Å] and a very short c [5.36308 (13) Å] unit‐cell parameter (hexagonal setting). The detailed analysis of the intermolecular interactions observed in the crystal structure of 1 highlights its potential towards the implementation of this core as a semiconductor in organic thin‐film transistor (OTFT) devices. Since the molecule has a flat configuration reflecting its π‐conjugated system, neighbouring molecules are found to stack atop each other in a slipped parallel fashion via π–π stacking interactions between planes of ca 3.30 Å, with a centroid–centroid distance between the aromatic rings corresponding to the shortest axis of the unit cell ( i.e. c ). The alkylation of the three N atoms proves to be a decisive feature since it favours the presence of C—H…π interactions in all directions, which strengthens the crystal packing. As a whole, PXRD proves to be a valuable option for the resolution of otherwise inaccessible organic crystal structures of interest in different areas.