Cover Image

Pentacene to octacene: the limit of fourfold TIPS-ethynylation

<p>Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4 + 4] dimerization and oxidation. At the same time, such acenes...

Full description

Saved in:
Bibliographic Details
Main Authors: Zeitter, Nico (Author) , Hippchen, Nikolai (Author) , Baur, Philipp (Author) , Unterreiner, Tamara (Author) , Rominger, Frank (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: 01 Februar 2024
In: Organic materials
Year: 2024, Volume: 6, Issue: 1, Pages: 12-17
ISSN:2625-1825
DOI:10.1055/a-2241-0243
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1055/a-2241-0243
Verlag, kostenfrei, Volltext: http://www.thieme-connect.de/DOI/DOI?10.1055/a-2241-0243
Get full text
Author Notes:Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara V. Unterreiner, Frank Rominger, Jan Freudenberg, Uwe H. F. Bunz
Description
Summary:<p>Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4 + 4] dimerization and oxidation. At the same time, such acenes are soluble and processible. Here we present the modular synthesis of fourfold tri-<i>iso</i>-propylsilylethynyl-ethynylated pentacenes to octacenes and investigate their optical and redox properties, frontier orbital positions (CV, density functional theory calculations) as well as their stability in solution (UV/vis, NMR spectroscopy). We also investigated their magnetic properties as a function of acene length. Pentacene, hexacene and heptacene are sufficiently stable to serve as semiconductors in thin-film transistors - the octacene rapidly decays to its butterfly dimer evidence by time-dependent NMR spectroscopy and crystal structure analysis.</p>
Item Description:Gesehen am 14.03.2024
Physical Description:Online Resource
ISSN:2625-1825
DOI:10.1055/a-2241-0243

Similar Items