Synthesis of a 4,9-Didodecyl Angular-Shaped Naphthodiselenophene Building Block To Achieve High-Mobility Transistors

Abstract

A new tetracyclic 4,9-dialkyl angular-shaped naphthodiselenophene (4,9-α-aNDS) was designed and synthesized. The naphthalene core in 4,9-α-aNDS is formed by the DBU-induced 6π-cyclization of an (E)-1,2-bis(3-(tetradec-1-yn-1-yl)selenophen-2-yl)ethene intermediate followed by the second PtCl 2 -catalyzed benzannulation. This synthetic protocol allows for incorporating two dodecyl groups regiospecifically at 4,9-positions of the resulting α-aNDS. An ordered supramolecular self-assembly formed via noncovalent selenium−selenium interactions with a short contact of 3.5 Å was observed in the single-crystal structure of 4,9-α-aNDS. The distannylated α-aNDS building block was copolymerized with Br-DTFBT and Br-DPP acceptors by Stille cross coupling to form two new donor−acceptor polymers PαNDSDTFBT and PαNDSDPP, respectively. The bottom-gate/top-contact organic fieldeffect devices using the PαNDSDTFBT and PαNDSDPP semiconductors accomplished superior hole mobility of 3.77 and 2.17 cm 2 V −1 s −1 , respectively, which are among the highest mobilities reported to date.

Multifluorination toward High‐Mobility Ambipolar and Unipolar n‐Type Donor–Acceptor Conjugated Polymers Based on Isoindigo

“…In past several years, incorporating F atoms into conjugated backbone has emerged as a protocol to lower HOMO and LUMO energy levels and enhance the coplanarity of CPs, and various high‐mobility D–A CPs containing F atoms on either D or A units have been reported . In the current paper, we demonstrated that “multifluorination”, i.e., introducing F atoms onto both D and A units, not only can greatly lower the frontier orbital energy levels of the IID‐based polymers, but also can enhance the coplanarity of their conjugated backbones.…”

Stacking Principles on π- and Lamellar Stacking for Organic Semiconductors Evaluated by Energy Decomposition Analysis

“…Because traditional density functionals often fail in describing the dispersion force accurately, an additional dispersion correction ( E dis ) can be included in the above energy decomposition scheme with the aim of taking long-range interactions into consideration. 48−56 Herein, numerous N , N ′-dialkyl-1,4,5,8-naphthalenetetracarboxylic diimides (R-NDIs) are chosen for the study, such as R = C 14 H 29 , 57 C 12 H 25 , 58 C 6 H 13 , 59 C 5 H 11 , 60 C 4 H 9 , 58 C 2 H 5 , 61 and 1-CH 3 C 6 H 12 58 (Scheme 2). The π- and lamellar stacking extracted from selected single-crystal structures are examined by ETS–NOCV.…”

A Critical Review on Efficient Thick‐Film Organic Solar Cells

“…Compared with thiophene, the lower aromatic selenophene can increase the quinoidal resonance content, leading to an enhanced planarity of structures and lower optical bandgap. [ 110,111 ] The selenophene‐containing NFAs may be promising candidates for preparing efficient thick‐film OSCs. Hou and coworkers developed an efficient NFA, SeTIC4Cl, which contains selenopheno[3,2‐b]thiophene‐embedded seven‐heterocyclic fused ring core and dichlorinated end‐capped units.…”