In:
Angewandte Chemie, Wiley, Vol. 135, No. 34 ( 2023-08-21)
Abstract:
A family of novel highly π‐extended tetracyano‐substituted acene diimides, named as tetracyanodiacenaphthoanthracene diimides (TCDADIs), have been synthesized using a facile four‐fold Knoevenagel condensation strategy. Unlike conventional cyano substitution reactions, our approach enables access to a large π‐conjugated backbone with the in‐situ formation of four cyano substitutents at room temperature while avoiding extra cyano‐functionalization reactions. TCDADIs decorated with different N‐alkyl substituents present good solubility, near‐coplanar backbones, good crystallinity, and low‐lying lowest unoccupied molecular orbital energies of −4.33 eV, all of which contribute to desirable electron‐transport performance when applied in organic field‐effect transistors (OFET). The highest electron mobility of an OFET based on a 2‐hexyldecyl‐substituted TCDADI single crystal reaches 12.6 cm 2 V −1 s −1 , which is not only among the highest values for the reported n‐type organic semiconductor materials (OSMs) but also exceeds that of most n‐type OSMs decorated with imide units.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.34
DOI:
10.1002/ange.202307695
Language:
English
Publisher:
Wiley
Publication Date:
2023
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