Detail publikace

Effect of the ethynylene linker on the properties and carrier mobility of naphthalene derivatives with hexylbithienyl arms

Originální název

Effect of the ethynylene linker on the properties and carrier mobility of naphthalene derivatives with hexylbithienyl arms

Anglický název

Effect of the ethynylene linker on the properties and carrier mobility of naphthalene derivatives with hexylbithienyl arms

Jazyk

en

Originální abstrakt

A series of new naphthalene derivatives with (50-hexyl-2,20-bithiophene-5-yl)ethynyl side arms attached to the central naphthalene core at positions 1 and 4 (H2TA14N), 1 and 5 (H2TA15N), and 2 and 6 (H2TA26N) were synthesized by a sequencing of alkynylations performed according to a Negishi crosscoupling protocol. This synthetic approach provides higher yields compared to Sonogashira-based alkynylations, particularly when aryl bromides are used as starting materials. Compared to the analogous derivatives with hexylbithienyl arms directly attached to the naphthalene core (H2T14N,H2T15N, and H2T26N), an ethynylene linker ensures the planarity of the molecules, causing a change in the order of derivatives by intramolecular conjugation from H2T15N < H2T14N < H2T26N to H2TA15N ~ H2TA26N < H2TA14N, as can be seen from the solution, and thin film optical and electrochemical properties as well. However, the order of derivatives by the hole mobility in a field effect transistor remains unaltered by an ethynylene linker (H2TA14N < H2TA15N < H2TA26N). The tendency in charge mobility can be explained by different packing motifs affected by molecular symmetry and was revealed by single crystal X-ray analysis and 2D X-ray GIWAXS and AFM characterization of the thin films.

Anglický abstrakt

A series of new naphthalene derivatives with (50-hexyl-2,20-bithiophene-5-yl)ethynyl side arms attached to the central naphthalene core at positions 1 and 4 (H2TA14N), 1 and 5 (H2TA15N), and 2 and 6 (H2TA26N) were synthesized by a sequencing of alkynylations performed according to a Negishi crosscoupling protocol. This synthetic approach provides higher yields compared to Sonogashira-based alkynylations, particularly when aryl bromides are used as starting materials. Compared to the analogous derivatives with hexylbithienyl arms directly attached to the naphthalene core (H2T14N,H2T15N, and H2T26N), an ethynylene linker ensures the planarity of the molecules, causing a change in the order of derivatives by intramolecular conjugation from H2T15N < H2T14N < H2T26N to H2TA15N ~ H2TA26N < H2TA14N, as can be seen from the solution, and thin film optical and electrochemical properties as well. However, the order of derivatives by the hole mobility in a field effect transistor remains unaltered by an ethynylene linker (H2TA14N < H2TA15N < H2TA26N). The tendency in charge mobility can be explained by different packing motifs affected by molecular symmetry and was revealed by single crystal X-ray analysis and 2D X-ray GIWAXS and AFM characterization of the thin films.

BibTex


@article{BUT127461,
  author="Stanislav {Stříteský} and Martin {Vala} and Martin {Weiter}",
  title="Effect of the ethynylene linker on the properties and carrier mobility of
naphthalene derivatives with hexylbithienyl arms",
  annote="A series of new naphthalene derivatives with (50-hexyl-2,20-bithiophene-5-yl)ethynyl side arms attached to the central naphthalene core at positions 1 and 4 (H2TA14N), 1 and 5 (H2TA15N), and 2 and 6 (H2TA26N) were synthesized by a sequencing of alkynylations performed according to a Negishi crosscoupling protocol. This synthetic approach provides higher yields compared to Sonogashira-based alkynylations, particularly when aryl bromides are used as starting materials. Compared to the analogous derivatives with hexylbithienyl arms directly attached to the naphthalene core (H2T14N,H2T15N, and H2T26N), an ethynylene linker ensures the planarity of the molecules, causing a change in the order of derivatives by intramolecular conjugation from H2T15N < H2T14N < H2T26N to H2TA15N ~ H2TA26N 
< H2TA14N, as can be seen from the solution, and thin film optical and electrochemical properties as well. However, the order of derivatives by the hole mobility in a field effect transistor remains unaltered by an ethynylene linker (H2TA14N < H2TA15N < H2TA26N). The tendency in charge mobility can be explained by different packing motifs affected by molecular symmetry and was revealed by single crystal X-ray analysis and 2D X-ray GIWAXS and AFM characterization of the thin films.",
  address="Elsvier - Synthetic Metals",
  chapter="127461",
  doi="10.1016/j.synthmet.2016.03.034",
  howpublished="online",
  institution="Elsvier - Synthetic Metals",
  number="217",
  volume="2016",
  year="2016",
  month="april",
  pages="156--171",
  publisher="Elsvier - Synthetic Metals",
  type="journal article in Web of Science"
}