Indene‐Based Donor‐Acceptor Type Small Molecular Semiconductors for High‐Performance n‐Channel Transistors

Abstract

It is a great challenge to design n-channel donor-acceptor (DÀ A) type small molecules because of the lack of strong electron withdrawing acceptor unit. Herein, 3-(dicyanomethylidene)-indan-1-one (IC) and 1,3-bis(dicyanomethylidene)-indene (IDC) based DÀ A type small molecular organic semiconductors IC-DDTPTI and IDC-DDTPTI are synthesized and characterized. Both compounds have low-lying LUMO energy levels, especially for IDC-DDTPTI with LUMO energy level lower than À 4.0 eV.Thin film transistor characteristics show IC-DDTPTI displays ambipolar transistor behavior with balanced hole and electron mobility. The electron mobility is 0.40 cm 2 V À 1 s À 1 and the hole mobility reaches 0.18 cm 2 V À 1 s À 1 . IDC-DDTPTI exhibits unipolar n-channel character with an electron mobility of 0.027 cm 2 V À 1 s À 1 . These results highlight the applications of IC and IDC units in high performance DÀ A type n-channel organic semiconductors.

End-Capping π-Conjugated Naphthodithiophene Diimide (NDTI)-Based Triads with Noncovalent Intramolecular S···O Interactions: A Route towards High-Performance Solution-Processable Air-Stable n-Type Semiconductors

“…In addition, in order to construct unipolar n-type semiconductor materials, electron-deficient groups are introduced into NDTI to reduce the LUMO energy level of the corresponding compound and promote effective electron injection. Among these, 3-(dicyanomethylidene)-indan-1-one (IC) as a strong electron-deficient group has been widely used in recent years. − Herein, we report two new NDTI-based small molecules ( NDTI-BTIC1 and NDTI-BTIC2 , Figure c) covalently connected by an electron-deficient NDTI-core and two 3-(dicyanomethylidene)-indan-1-one (IC) groups with alkoxy chain- or alkyl chain-substituted thiophene as bridging groups, respectively. Compared with the analogue NDTI-BTIC2 , NDTI-BTIC1 possesses a completely coplanar molecular structure, possibly attributed to noncovalent intramolecular S (thiophene)···O (alkoxy) interactions, which is proved by density functional theory (DFT) calculations.…”

Maghnite‐H+ Catalytic Synthesis and Characterization of Polyindenes and Oxidized Derivatives

“…Besides, the extended π‐conjugation, coplanarity and the presence of polarons have been proposed to be responsible of the electrical conductivity in this system, showing values ranging from 1.1*10 −5 to 7.9*10 −4 S cm −1 . Accordingly, PIns find potential application in areas such as solar energy systems, (photo)electronics, electrochromic devices, etc., apart from thermoplastics industry or gas separation . On the other hand, chemical modifications of PIns via sulfonation or hydrogenation have been studied to obtain polymers for proton‐exchange membrane fuel cells (PEMFCs) and/or with interesting thermal properties, respectively.…”