Synthesis and Electrochromic Properties of Thiophene-carbazol-benzene Derivativies†

doi:10.7503/cjcu20170837

Abstract

Abstract:

The central phenyl and biphenyl groups were introduced into the N-positions of two thiophene-carbazole structures to form the desired 9,9'-(1,4-phenylene)bis[3,6-di-2-thienyl]-9H-carbazole(BTCPh) and 9,9'-[1,1'-biphenyl]-4,4'-diylbis[3,6-di-2-thienyl]-9H-carbazole(BTCBPh), respectively. The obtained BTCPh and BTCBPh were electrochemically polymerized to generate the corresponding polymers, poly 9,9'-(1,4-phenylene)bis[3,6-di-2-thienyl]-9H-carbazole(pBTCPh) and poly 9,9'-[1,1'-biphenyl]-4,4'-diylbis[3,6-di-2-thienyl]-9H-carbazole(pBTCBPh), which might possess the cross-linked structure. The polymers were investigated by different character methods, such as cyclic voltammetry, multi-current step, ultraviolet visible near infrared absorption spectrum, scanning electron microscope and so on. The results showed that both of pBTCPh and pBTCBPh polymers exhibited excellent electrochromic properties with similar color changes, high optical contrast and good electrochemical cycle stability. And pBTCPh polymer film showed the faster color switching speed than pBTCBPh, which was ascribed to the possible more uniform stack structure in pBTCPh film. The uniform stack structure was beneficial to the fast ion inserting/deserting behavior in the electrochromic process.

Key words: Thiophene-carbazole derivative, Electrochromic color, Packing structure, Response time

CLC Number:

O622
O646

TrendMD:

QU Xingxing, DAI Yuyu, LI Weijun, OUYANG Mi, ZHANG Cheng. Synthesis and Electrochromic Properties of Thiophene-carbazol-benzene Derivativies^†[J]. Chem. J. Chinese Universities, 2018, 39(8): 1699.

Figures/Tables 10

Scheme 1 Synthetic route of BTCPh(n=1) and BTCBPh(n=2) and possible cross-linked structure of pBTCPh(n=1) and pBTCBPh(n=2)

Fig.1 Cyclic voltammetric curves of BTCPh(a) and BTCBPh(b) in DCM/ACN(volume ratio 9:1) solution containing 0.1 mol/L TBAP at a scan rate of 100 mV/s

Fig.2 UV-Vis absorption spectra of BTCPh(a) and BTCBPh(b) in DCM solution

Fig.3 Cyclic voltammetric curves(10 cycles) for polymerization of BTCPh(A) and

Fig.4 Cyclic voltammetric curves of pBTCPh(A) and pBTCBPh(B) in monomer free acetonitrile solution containing 0.1 mol/L TBAPScan rate from 50 mV/s to 200 mV/s, insets of (A) and (B) are the curves of pBTCPh and pBTCBPh of its redox peak current value versus scan rate, respectivley.

Fig.5 UV-Vis-NIR absorbance curves of pBTPh(A) and pBTCBPh(B) polymers in applied potential of 0—1.2 VInsets are the UV-Vis absorbance curves of pBTCPh and pBTCBPh polymers upon 0 V.

Fig.6 Optical contrast of pBTCPh(A) and pBTCBPh(B) polymers films

Fig.7 Switching time monitored at 410(A), 660(B) and 1100 nm(C) in acetonitrile solution containing 0.1 mol/L TBAP between 0 and 1.2 V with residence time of 10 sa. pBTCPh; b. pBTCBPh.

Fig.8 SEM images of pBTCPh(A) and pBTCBPh(B) polymer films

Fig.9 Cycle stability of pBTCPh(A) and pBTCBPh(A) polymers films

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