Thiophene-containing organic semiconducting heteroacenes for electronic applications [Elektronische Ressource] / Peng Gao

Fishyu

Informations

• Publié par: johannes_gutenberg-universitat_mainz
• Publié le: 01 janvier 2009
• Nombre de lectures: 91
• Langue: English
• Poids de l'ouvrage: 9 Mo

Extrait

Thiophene-Containing Organic
Semiconducting Heteroacenes for
Electronic Applications


Dissertation





zur Erlangung des Grades
‘Doktor der Naturwissenschaften’

am Fachbereich Chemie und Pharmazie der
Johannes Gutenberg-Universität in Mainz



Peng Gao
Geboren in Shanxi Province / China
Mainz 2009



































Dekan:
1. Berichterstatter:
2. Berichterstatter:
Tag der mündlichen Prüfung: 17, Feb. 2010






Dedicated to my family
Table of Contents
List of Figures ······················································································································ vi
List of Schemes ··················································································································· xv
List of Tables ···················································································································· xvii
Glossary of Abbreviations ···························································································· xviii
Chapter 1 Introduction and Motivation ············································································· 1
1.1 Semiconducting materials for organic field-effect transistors (OFETs) ············· 1
1.1.1 Oligoacenes vs. conjugated polymers ........................................................... 4
1.1.2 PAH acenes and heteroacenes ........................................................................ 5
1.1.2.1 Why heteroacenes? ·················································································· 5
1.1.2.2 p-Channel heteroacenes ··········································································· 7
1.1.2.3 n-Channel heteroacenes8
1.2 Design principles of high performance oligoacenes ············································ 9
1.2.1 Energy levels of organic semiconductors ...................................................... 9
1.2.2 Tuning the HOMO level of p-channel oligoacenes .................................... 11
1.2.3 Tuning the LUMO level of n12
1.3 A summary of synthetic methods toward thiophene containing heteroacenes
········································································································································ 13
1.3.1 Synthesis of thiophene containing heteroacenes by sulfur-bridge
formation ................................................................................................................... 14
1.3.1.1 Formation of sulfur-bridges by triflic acid induced electrophilic
substitution ········································································································ 14
1.3.1.2 Introducation of thiophene rings by aromatic nucleophilic substitution
(S Ar) reaction ·································································································· 17 N
1.3.1.3 Introduction of thiophene rings by electrophilic cyclization reaction ···· 19
1.3.1.4 Intro thiophene ring by Hinsburg thiophene synthesis ··········· 20
1.3.2 Synthesis of thiophene containing heteroacenes by direct annulation of
thiophene units ........................................................................................................ 21
1.3.2.1 Friedel-Crafts-type alkylation and acylation reactions ·························· 21
i 1.3.2.2 Cadogan reductive cyclization on thiophene units ································· 23
1.4 Solid-state structure of full ladder oligoacenes ·······································