2 research outputs found
Synthesis, Structural Characterization, and Field-Effect Transistor Properties of <i>n</i>‑Channel Semiconducting Polymers Containing Five-Membered Heterocyclic Acceptors: Superiority of Thiadiazole Compared with Oxadiazole
Five-membered
1,3,4-oxadiazole (OZ) and 1,3,4-thiadiazole (TZ) heterocycle-based
copolymers as active layer have long been ignored in solution-processable <i>n</i>-channel polymer field-effect transistors (PFETs) despite
the long history of using OZ or TZ derivatives as the electron-injecting
materials in organic light-emitting devices and their favorable electron
affinities. Herein, we first report the synthesis and PFETs performance
of two <i>n</i>-channel conjugated polymers bearing OZ-
or TZ-based acceptor moieties, i.e., PNOZ and PNTZ, where simple thiophene
units are utilized as the weak donors and additional alkylated-naphthalenediimides
units are used as the second acceptors. A comparative study has been
performed to reveal the effect of different heterocyclic acceptors
on thermal properties, electronic properties, ordering structures,
and carrier transport performance of the target polymers. It is found
that both polymers possess low-lying LUMO values below −4.0
eV, indicating high electron affinity for both heterocycle-based polymers.
Because of strong polarizable ability of sulfur atom in TZ heterocycle,
PNTZ exhibits a red shift in maximal absorption and stronger molecular
aggregation even in the diluted chlorobenzene solution as compared
to the OZ-containing PNOZ. Surface morphological study reveals that
a nodule-like surface with a rough surface morphology is observed
clearly for PNOZ films, whereas PNTZ films display highly uniform
surface morphology with well interconnected fiber-like polycrystalline
grains. Investigation of PFETs performance indicates that both polymers
afford air-stable <i>n</i>-channel transport characteristics.
The uniform morphological structure and compact π–π
stacking endow PNTZ with a high electron mobility of 0.36 cm<sup>2</sup> V<sup>–1</sup> s<sup>–1</sup>, much higher than that
of PNOZ (0.026 cm<sup>2</sup> V<sup>–1</sup> s<sup>–1</sup>). These results manifest the feasibility in improving electron-transporting
property simply by tuning heteroatom substitutes in <i>n</i>-channel polymers; further demostrate that TZ derivatives possess
much superior potential for developing high-performance <i>n</i>-channel polymers compared to OZ derivatives
Directed Metalation Cascade To Access Highly Functionalized Thieno[2,3‑<i>f</i>]benzofuran and Exploration as Building Blocks for Organic Electronics
A tandem directed metalation has been successfully applied to the
preparation of thieno[2,3-<i>f</i>]benzofuran-4,8-dione,
providing an efficient and facile approach to symmetrically and unsymmetrically
functionalize the thieno[2,3-<i>f</i>]benzofuran core at
the 2,6 positions as well as to introduce the electron-withdrawing
or -donating groups (EWG or EDG) at its 4,8 positions. The presence
of various functional groups makes late-stage derivatization attainable