Peripherally Cyanated Subphthalocyanines as Potential n‐Type Organic Semiconductors

A series of peripherally dicyano‐, tricyano‐, and tetracyano‐substituted subphthalocyanines (SubPcs) have been prepared through microwave‐assisted, palladium‐mediated cyanation of iodinated precursors. The introduction of π‐accepting cyano groups in the macrocycle clearly influences its electronic a...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-06, Vol.24 (33), p.8331-8342
Main Authors: Zango, Germán, Sakurai, Tsuneaki, Urones, Beatriz, Saeki, Hidenori, Matsuda, Wakana, Martínez‐Díaz, M. Victoria, Seki, Shu, Torres, Tomás
Format: Article
Language:English
Subjects:
charge transfer
Chemistry
Current carriers
Cyano groups
Electronics industry
Energy levels
Fabrication
Flash photolysis
Organic semiconductors
Palladium
photochemistry
Photolysis
Photovoltaic cells
Photovoltaics
Redox properties
Semiconductors
Solar cells
subphthalocyanines
substituent effects
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Summary:A series of peripherally dicyano‐, tricyano‐, and tetracyano‐substituted subphthalocyanines (SubPcs) have been prepared through microwave‐assisted, palladium‐mediated cyanation of iodinated precursors. The introduction of π‐accepting cyano groups in the macrocycle clearly influences its electronic and redox properties, which are dependent on the number and relative position of these substituents. Additional functionalization of the periphery of SubPcs with electron‐donating or ‐withdrawing groups allows for a further fine‐tuning of their features, leading to intensely absorbing, strongly electron‐accepting panchromatic dyes with low‐lying LUMO energy levels. Flash‐photolysis time‐resolved microwave conductivity measurements on vapor‐deposited films demonstrate that some of these novel SubPc derivatives display remarkable intrinsic charge‐carrier mobilities that are comparable to or larger than those of other known well‐performing acceptor SubPcs; thus confirming their potential as n‐type organic semiconductors for application in the fabrication of photovoltaic devices. On the edge: Peripherally cyanated subphthalocyanines (SubPcs) additionally functionalized with either electron‐donating or ‐withdrawing groups have been synthesized, leading to intensely absorbing, strongly electron‐accepting panchromatic dyes with low‐lying LUMO energy levels (see figure). These SubPcs display remarkable intrinsic charge carrier mobilities for potential application as n‐type organic semiconductors.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201801190