Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Viktor Barát; Maja Budanovic; Si Man Tam; June Huh; Richard D. Webster; Mihaiela C. Stuparu

doi:10.1002/chem.201905521

Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Viktor Barát, Maja Budanovic, Si Man Tam, June Huh, Richard D. Webster, Mihaiela C. Stuparu

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C₁₈H₃₇) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.

Original language	English
Pages (from-to)	3231-3235
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	15
DOIs	https://doi.org/10.1002/chem.201905521
Publication status	Published - 2020 Mar 12

Keywords

corannulene
electron-deficient compounds
fused-ring systems
polycyclic aromatic hydrocarbons
sulfones

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201905521

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title = "Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility",

abstract = "It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C18H37) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.",

keywords = "corannulene, electron-deficient compounds, fused-ring systems, polycyclic aromatic hydrocarbons, sulfones",

author = "Viktor Bar{\'a}t and Maja Budanovic and Tam, {Si Man} and June Huh and Webster, {Richard D.} and Stuparu, {Mihaiela C.}",

note = "Funding Information: Financial support from the Ministry of Education Singapore under the AcRF Tier 1 (MOE2017‐T1‐001‐17, M4011792) (2018‐T1‐001‐176, M4012047); Agency for Science, Technology and Research (A*STAR)‐AME IRG A1883c0006; and NTU (M4081566) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = mar,

day = "12",

doi = "10.1002/chem.201905521",

language = "English",

volume = "26",

pages = "3231--3235",

journal = "Chemistry - A European Journal",

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T1 - Corannulene-Based Electron Acceptors

T2 - Combining Modular and Practical Synthesis with Electron Affinity and Solubility

AU - Barát, Viktor

AU - Budanovic, Maja

AU - Tam, Si Man

AU - Huh, June

AU - Webster, Richard D.

AU - Stuparu, Mihaiela C.

N1 - Funding Information: Financial support from the Ministry of Education Singapore under the AcRF Tier 1 (MOE2017‐T1‐001‐17, M4011792) (2018‐T1‐001‐176, M4012047); Agency for Science, Technology and Research (A*STAR)‐AME IRG A1883c0006; and NTU (M4081566) is gratefully acknowledged. Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/3/12

Y1 - 2020/3/12

N2 - It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C18H37) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.

AB - It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C18H37) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.

KW - corannulene

KW - electron-deficient compounds

KW - fused-ring systems

KW - polycyclic aromatic hydrocarbons

KW - sulfones

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EP - 3235

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 15

ER -

Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Abstract

Keywords

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