Evidence map›Paper›PMID 32510761›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Unilaterally Fluorinated Acenes: Synthesis and Solid-State Properties.

Philipp E Hofmann, Matthias W Tripp, Daniel Bischof, Yvonne Grell, Anna L C Schiller, Tobias Breuer, Sergei I Ivlev, Gregor Witte, Ulrich Koert

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

8 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Diazapentacenes from Quinacridones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021
    Article
  5. Article
  6. Unilaterally Fluorinated Acenes: Synthesis and Solid-State Properties.Angewandte Chemie (International ed. in English) · 2020
    Article
  7. Article
  8. Synthesis of 6,13-difluoropentacene.Beilstein journal of organic chemistry · 2020
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

9 authors.

Philipp E HofmannFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.
Matthias W TrippFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.
Daniel BischofFachbereich Physik, Philipps-Universität Marburg, Renthof 7, 35032, Marburg, Germany.
Yvonne GrellFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.
Anna L C SchillerFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.
Tobias BreuerFachbereich Physik, Philipps-Universität Marburg, Renthof 7, 35032, Marburg, Germany.
Sergei I IvlevFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.
Gregor WitteFachbereich Physik, Philipps-Universität Marburg, Renthof 7, 35032, Marburg, Germany.ORCID http://orcid.org/0000-0003-2237-0953
Ulrich KoertFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.ORCID http://orcid.org/0000-0002-4776-8549

Funding

Deutsche Forschungsgemeinschaft SFB 1083, TP A2Deutsche Forschungsgemeinschaft SFB 1083 TP A8
6 · The paper itself

Abstract

The rapid development of organic electronics is closely related to the availability of molecular materials with specific electronic properties. Here, we introduce a novel synthetic route enabling a unilateral functionalization of acenes along their long side, which is demonstrated by the synthesis of 1,2,10,11,12,14-hexafluoropentacene (1) and the related 1,2,9,10,11-pentafluorotetracene (2). Quantum chemical DFT calculations in combination with optical and X-ray absorption spectroscopy data indicate that the single-molecule properties of 1 are a connecting link between the organic semiconductor model systems pentacene (PEN) and perfluoropentacene (PFP). In contrast, the crystal structure analysis reveals a different packing motif than for the parent molecules. This can be related to distinct F⋅⋅⋅H interactions identified in the corresponding Hirshfeld surface analysis and also affects solid-state properties such as the exciton binding energy and the sublimation enthalpy.

Indexed as

aceneselectronic structurefluorinated acenessolid-state structuresunilateral substitution

Identifiers

PMID32510761
PMCPMC7540388

What OpenQuestion holds

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.