Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Acid dyeing for green solvent processing of solvent resistant semiconducting organic thin films

Author affiliations

Abstract

The alcohol and water-based processing of a perylene diimide (PDI) organic semiconductor into large area and solvent resistant films is reported. The compound, PDIN-H, is an N-annulated PDI dye with a pyrrolic NH functional group that can be deprotonated to render the material soluble in polar solvents. Addition of NaOH to mixtures of PDIN-H in 1-propanol results in a progressive color change from orange/red to purple with increasing equivalents of base. Use of 1 molar equivalent of NaOH was found to fully dissolve the PDIN-H in alcohol solvents up to a concentration of 10 mg mL−1. Primary alcohols 1-propanol to 1-hexanol as well as 2-propanol were used. All solutions were readily spin-coated or slot-die coated into uniform thin films. Solutions in 1-propanol could be coated with concentrations up to 50 mg mL−1. All films were red in color and characterized by optical absorption spectroscopy confirming the existence of the parent PDIN-H species in the film. Single crystal X-ray diffraction was used to determine the molecular packing of PDIN-H. Films showed no signs of dewetting, swelling, or dissolution upon exposure to 2-propanol, water, or o-xylene via coating or dipping indicating they were solvent resistant. To exploit the semiconducting properties of these PDIN-H films, organic photovoltaic devices were fabricated using the films as electron transport layers in inverted type P3HT:PC61BM bulk heterojunction devices. Moreover, the PDIN-H films changed from red to purple upon exposure to butylamine vapors which prompted the investigation of hydroxide free processing. Indeed, films of PDIN-H were easily formed by processing with 1-propanol/butylamine or water/butylamine solutions.

Graphical abstract: Acid dyeing for green solvent processing of solvent resistant semiconducting organic thin films

Back to tab navigation

Supplementary files

Article information


Submitted
11 May 2020
Accepted
20 Aug 2020
First published
20 Aug 2020

Mater. Horiz., 2020, Advance Article
Article type
Communication

Acid dyeing for green solvent processing of solvent resistant semiconducting organic thin films

C. R. Harding, J. Cann, A. Laventure, M. Sadeghianlemraski, M. Abd-Ellah, K. R. Rao, B. S. Gelfand, H. Aziz, L. Kaake, C. Risko and G. C. Welch, Mater. Horiz., 2020, Advance Article , DOI: 10.1039/D0MH00785D

Social activity

Search articles by author

Spotlight

Advertisements