Incorporation of 2,6‐Connected Azulene Units into the Backbone of Conjugated Polymers: Towards High‐Performance Organic Optoelectronic Materials

Abstract

Azulene is ap romising candidate for constructing optoelectronic materials.A ne ffective strategy is presented to obtain high-performance conjugated polymers by incorporating 2,6-connected azulene units into the polymeric backbone, and two conjugated copolymers P(TBAzDI-TPD) and P(TBAzDI-TFB) were designed and synthesized based on this strategy.They are the first two examples for 2,6-connected azulene-based conjugated polymers and exhibit unipolar ntype transistor performance with an electron mobility of up to 0.42 cm 2 V À1 s À1 ,w hich is among the highest values for n-type polymeric semiconductors in bottom-gate top-contact organic field-effect transistors.P reliminary all-polymer solar cell devices with P(TBAzDI-TPD) as the electron acceptor and PTB7-Th as the electron donor displayapower conversion efficiency of 1.82 %.

Development of Heterocycle-Substituted and Fused Azulenes in the Last Decade (2010–2020)

“…Gao and colleagues have prepared diimide derivatives based on 2,2′-biazulene and demonstrated their optical and electrochemical properties ( Scheme 54 ) [ 76 ]. 2,2′-Biazulene-1,1′,3,3′-tetracarboxylic diimides (BAZDIs 162 and 164 ) are synthesized by aminolysis of acid anhydrides 161 and 163 , followed by dehydration with SOCl 2 .…”

Imide‐Functionalized Polymer Semiconductors

“…When appliedi nt he OTFTs, 74 showedaunipolar m e,OTFT of 0.24 cm 2 V À1 s À1 after annealing at 200 8Ca nd 73 exhibited an increased m e,OTFT of 0.42 cm 2 V À1 s À1 with ah igh I on /I off ratio of 10 5 -10 6 .A ll-PSC cells were fabricated by using the D1:73 blend as the active layer and showed a PCE of 1.82 %. [84] Jiang and our group independently developed af used diimide electron-deficient unit, dithienylbenzodiimide (TBDI), in which ac entral phenyl ring was fused with two adjacent thiophenesf eaturing imide-containingh eptacyclic rings. [85] When copolymerized with various donor co-units, such as thiophene, bithiophene, difluorobithiophene, as eries of polymer semiconductors, 75, 76,a nd 77,w ere synthesized with low-lying LUMOs in the range of approximately À3.65 to À3.78 eV, [a] Opticalb and gap estimated from the absorptiononset of thin films.…”

Synthesis of Azulenopyridinones through Palladium‐Catalyzed Oxidative [4+2] Cyclization Reactions of N‐Methoxyazulene‐1‐ and 2‐carboxamides with Alkynes

“…Azulenes, which are a class of nonbenzenoid aromatic hydrocarbons, have received prominent attention due to their importance as natural products, [1] bioactive compounds, [2] and molecular materials. [3] Accordingly, the establishment of streamlined synthetic approaches for azulene skeletons from easily accessible starting materials is continuously required. [4] Hafner and coworkers described an efficient method for azulene synthesis.…”