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Title: An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors

Journal Article · · Chemistry - A European Journal
 [1];  [2]; ORCiD logo [1];  [1];  [1];  [3];  [3];  [4];  [2];  [1];  [2];  [1]
  1. Soochow Univ., Suzhou (China). Inst. of Functional Nano & Soft Materials (FUNSOM)
  2. Peking Univ., Beijing (China). Beijing National Lab. for Molecular Sciences, Key Lab. of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Key Lab. of Polymer Chemistry and Physics of Ministry of Education, Center for Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS)
  4. Argonne National Lab. (ANL), Lemont, IL (United States). Science Div.
+ Show Author Affiliations

A new electron-deficient unit with fused 5-heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with cyclohepta- 4,6-diene-1,3-diimde unit. The imide bridging endows BBI with fixed planar configuration and both low the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbit (LUMO) energy levels. Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm2 V-1 s-1, which indicates that the BBI is a promising ntype semiconductor for optoelectronics.

Research Organization:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division; National Natural Science Foundation of China (NSFC)
Grant/Contract Number:
AC05-00OR22725; AC02-06CH11357; 21504062; 21572152
OSTI ID:
1427654
Alternate ID(s):
OSTI ID: 1398725; OSTI ID: 1411169
Journal Information:
Chemistry - A European Journal, Vol. 23, Issue 59; ISSN 0947-6539
Publisher:
ChemPubSoc EuropeCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 12 works
Citation information provided by
Web of Science

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Cited By (2)

Imide‐Functionalized Polymer Semiconductors journal December 2018
Synthesis and characterization of new N-{4,6-bis[2-(het)arylvinyl]pyrimidin-2-yl}-substituted polycyclic aromatic imides journal September 2019

Linked Research (1)

Figures / Tables (6)

Figure 1(p. 2)figure Figure 1
Figure 2(p. 3)figure Figure 2
Scheme 1(p. 3)figure Scheme 1
Figure 3(p. 4)figure Figure 3
Figure 4(p. 4)figure Figure 4
Figure 5(p. 5)figure Figure 5

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77 NANOSCIENCE AND NANOTECHNOLOGY
36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
electron-deficiency
fused rings
imides
organic semiconductors
thiophenes
electron-deficient
imide
ladder-type