From Linear to Angular Isomers: Achieving Tunable Charge Transport in Single-Crystal Indolocarbazoles Through Delicate Synergetic CH/NHâ
â
â
π Interactions.
Angew Chem Int Ed Engl
; 57(29): 8875-8880, 2018 Jul 16.
Article
em En
| MEDLINE
| ID: mdl-29457325
ABSTRACT
Weak intermolecular interaction in organic semiconducting molecular crystals plays an important role in molecular packing and electronic properties. Here, four five-ring-fused isomers were rationally designed and synthesized to investigate the isomeric influence of linear and angular shapes in affecting their molecular packing and resultant electronic properties. Single-crystal field-effect transistors showed mobility order of 5,7-ICZ (3.61â
cm2 V-1 s-1 ) >5,11-ICZ (0.55â
cm2 V-1 s-1 ) >11,12-ICZ (ca. 10-5 â
cm2 V-1 s-1 ) and 5,12-ICZ (ca. 10-6 â
cm2 V-1 s-1 ). Theoretical calculations based on density functional theory (DFT) and polaron transport model revealed that 5,7-ICZ can reach higher mobilities than the others thanks to relatively higher hole transfer integral that links to stronger intermolecular interaction due to the presence of multiple NHâ
â
â
π and CHâ
â
â
π(py) interactions with energy close to common NHâ
â
â
N hydrogen bonds, as well as overall lower hole-vibrational coupling owing to the absence of coupling of holes to low frequency modes due to better π conjugation.
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MEDLINE
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En
Ano de publicação:
2018
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Article