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Phenylethenyl‐Substituted Triphenylamines: Efficient, Easily Obtainable, and Inexpensive Hole‐Transporting Materials
Author(s) -
Malinauskas Tadas,
Daskeviciene Maryte,
Bubniene Giedre,
Petrikyte Ieva,
Raisys Steponas,
Kazlauskas Karolis,
Gaidelis Valentas,
Jankauskas Vygintas,
Maldzius Robertas,
Jursenas Saulius,
Getautis Vytautas
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204064
Subject(s) - triphenylamine , quantum yield , materials science , intramolecular force , fluorescence , side chain , relaxation (psychology) , core (optical fiber) , glass transition , crystallinity , solid state , diffusion , quantum efficiency , chemical physics , optoelectronics , polymer , chemistry , optics , composite material , physics , stereochemistry , thermodynamics , psychology , social psychology
Star‐shaped charge‐transporting materials with a triphenylamine (TPA) core and various phenylethenyl side arm(s) were obtained in a one‐step synthetic procedure from commercially available and relatively inexpensive starting materials. Crystallinity, glass‐transition temperature, size of the π‐conjugated system, energy levels, and the way molecules pack in the solid state can be significantly influenced by variation of the structure of these side arm(s). An increase in the number of phenylethenyl side arms was found to hinder intramolecular motions of the TPA core, and thereby provide significant enhancement of the fluorescence quantum yield of the TPA derivatives in solution. On the other hand, a larger number of side arms facilitated exciton migration through the dense side‐arm network formed in the solid state and, thus, considerably reduces fluorescence efficiency by migration‐assisted nonradiative relaxation. This dense network enables charges to move more rapidly through the hole‐transport material layer, which results in very good charge drift mobility ( μ up to 0.017 cm 2 V −1 s −1 ).