Fully Conjugated Tri(perylene bisimides): An Approach to the Construction of n-Type Graphene Nanoribbons
- 26 November 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (52), 17970-17976
- https://doi.org/10.1021/ja807803j
Abstract
We present an experimental study encompassing synthesis and characterization of fully conjugated tri(perylene bisimides) (triPBIs), having 19 six-membered carbon rings in the core and six imide groups at the edges. Two structural isomers of triPBIs resulting from the two probable coupling positions were successfully separated by HPLC. To assist the identification of the two structural isomers, quantum-chemical calculations of electronic structure, NMR, and optical spectra were carried out. Calculations predict stable helical and nonhelical configurations for both triPBIs isomers and allow the assignment of triPBIs 6 unequivocally to the most bathochromically shifted absorption spectrum. Increasing the number of PBI units in oligo-PBIs leads to an expansion of the π system, in turn associated with a reduction of the transport and optical band gaps, and a remarkable increase in electron affinities, which make oligo-PBIs promising n-type functional components in optoelectronic devices.This publication has 51 references indexed in Scilit:
- Room-Temperature All-Semiconducting Sub-10-nm Graphene Nanoribbon Field-Effect TransistorsPhysical Review Letters, 2008
- Air-Stable n-Type Semiconductor: Core-Perfluoroalkylated Perylene BisimidesOrganic Letters, 2008
- Energy Band-Gap Engineering of Graphene NanoribbonsPhysical Review Letters, 2007
- The rise of grapheneNature Materials, 2007
- Photophysical and Electrochemical Properties of 1,7-Diaryl-Substituted Perylene DiimidesThe Journal of Organic Chemistry, 2005
- Perylene Bisimide Based Macrocycles: Effective Probes for the Assessment of Conformational Effects on Optical PropertiesAngewandte Chemie, 2004
- High‐Mobility Air‐Stable n‐Type Semiconductors with Processing Versatility: Dicyanoperylene‐3,4:9,10‐bis(dicarboximides)Angewandte Chemie-International Edition, 2004
- Interchain Interactions in Organic π-Conjugated Materials: Impact on Electronic Structure, Optical Response, and Charge TransportAdvanced Materials, 2001
- Electrochemistry, Spectroscopy and Electrogenerated Chemiluminescence of Perylene, Terrylene, and Quaterrylene Diimides in Aprotic SolutionJournal of the American Chemical Society, 1999
- Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculationsJournal of the American Chemical Society, 1990