Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks

The Effect of Star-Shaped versus Linear Conjugation on Their Electronic Structures

Alberto Riaño, Iratxe Arrechea-Marcos, María J. Mancheño, Paula MayorgaBurrezo, Alejandro delaPeña, Stephen Loser, Amod Timalsina, Antonio Facchetti, Tobin J Marks, Juan Casado, J. Teodomiro LópezNavarrete, Rocío PonceOrtiz, José L. Segura

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The synthesis, characterization, and optical properties of a novel star-shaped oligothiophene with a central rigid trithienobenzene (BTT) core and diketopyrrolopyrrole (DPP) units are reported and compared with homologous linear systems based on the benzodithiophene (BDT) and the naphthodithiophene (NDT) units end capped with DPPs. This comparison is aimed at elucidating the effect of the star-shaped configuration versus linear conformation on the optical and electrical properties. Electronic and vibrational spectroscopies, together with transient absorption spectroscopy, scanning electronic microscopy, and DFT calculations are used to understand not only the molecular properties of these semiconductors, but also to analyze the supramolecular aggregation in these derivatives. We conclude that although the subject star-shaped derivative is not optimal in terms of π-conjugation, its extended BTT unit significantly favors intermolecular π-stacking interactions, which is interesting for their applications in devices. Field-effect transistors and solar cells were fabricated with these new molecular semiconductors and the performance difference discussed.

Original languageEnglish
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2016

Fingerprint

Stars
Electronic structure
Optical properties
Semiconductor materials
Derivatives
Vibrational spectroscopy
Field effect transistors
Absorption spectroscopy
Discrete Fourier transforms
Linear systems
Conformations
Solar cells
Microscopic examination
Electric properties
Agglomeration
Scanning

Keywords

  • Field-effect transistors
  • Oligothiophene
  • Optical properties
  • Semiconductors
  • Solar cells
  • π-stacking interactions

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks : The Effect of Star-Shaped versus Linear Conjugation on Their Electronic Structures. / Riaño, Alberto; Arrechea-Marcos, Iratxe; Mancheño, María J.; MayorgaBurrezo, Paula; delaPeña, Alejandro; Loser, Stephen; Timalsina, Amod; Facchetti, Antonio; Marks, Tobin J; Casado, Juan; LópezNavarrete, J. Teodomiro; PonceOrtiz, Rocío; Segura, José L.

In: Chemistry - A European Journal, 2016.

Research output: Contribution to journalArticle

Riaño, A, Arrechea-Marcos, I, Mancheño, MJ, MayorgaBurrezo, P, delaPeña, A, Loser, S, Timalsina, A, Facchetti, A, Marks, TJ, Casado, J, LópezNavarrete, JT, PonceOrtiz, R & Segura, JL 2016, 'Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks: The Effect of Star-Shaped versus Linear Conjugation on Their Electronic Structures', Chemistry - A European Journal. https://doi.org/10.1002/chem.201504526
Riaño, Alberto ; Arrechea-Marcos, Iratxe ; Mancheño, María J. ; MayorgaBurrezo, Paula ; delaPeña, Alejandro ; Loser, Stephen ; Timalsina, Amod ; Facchetti, Antonio ; Marks, Tobin J ; Casado, Juan ; LópezNavarrete, J. Teodomiro ; PonceOrtiz, Rocío ; Segura, José L. / Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks : The Effect of Star-Shaped versus Linear Conjugation on Their Electronic Structures. In: Chemistry - A European Journal. 2016.
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