Synthesis and Multinuclear NMR Study on 2,6-Bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b´]dithiophene

Abstract

Abstract:

2,6-Bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b´]dithiophene, the monomer of a polymer solar cells material, was synthesized from 4,8-dihydrobenzo[1,2-b:4,5b´]dithiophen-4,8-dione. The structure of the compound was determined by multinuclear NMR spectroscopy, including ¹H, ¹³C, ¹¹⁹Sn, ¹¹⁷Sn NMR, DEPT, selective 1D TOCSY and 2D NMR techniques including ¹H-¹H COSY, gHSQC and gHMBC. The ¹H, ¹³C, ¹¹⁹Sn, ¹¹⁷Sn NMR chemical shifts were assigned and the spectral features of the compound were discussed.

Key words: NMR, assignment, ¹¹⁹Sn NMR, 2,6-bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b´]dithiophene, , polymer

CLC Number:

O482. 53

WANG Min-chang*，ZHANG Gao，XU Min，LIU Hong-li，LUAN Jie-yu，CHEN Zhi-qun，QI Zhu-chai. Synthesis and Multinuclear NMR Study on 2,6-Bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b´]dithiophene[J]. Chinese Journal of Magnetic Resonance.

References

[1] Gustafsson G, Cao Y, Treacy G M, et al. Flexible light-emitting-diodes from soluble conductingpolymers[J]. Nature, 1992, 357: 477-479.

[2] Yu G, Gao J, Hummelen J C, et al. Polymer photovoltaic cells: enhanced efficiencies via a network of internaldonor-acceptor heterojunctions[J]. Science, 1995, 270(5243): 1 789-1 791.

[3] Coakley K M, McGehee M D. Conjugated polymer photovoltaic cells[J]. Chem Mater, 2004, 16(23): 4 533-4 542.

[4] Kim J Y, Lee K, Coates N E, et al. Efficient tandem polymer solar cells fabricated by all-solution processing[J]. Science, 2007, 317: 222-225. 

[5] Blouin N, Michaud A, Gendron D, et al. Toward a rational design of poly (2,7-carbazole) derivatives for solar cells[J]. J Am Chem Soc, 2008, 130(2): 732-742.

[6] Hou J H, Chen H, Zhang S Q, et al. Synthesis and photovoltaic properties of two benzo [1,2-b∶3,4-b´] dithiophene-based conjugated polymers[J]. J Phys Chem C, 2009, 113: 21 202-21 207.

[7] Hou J H, Chen H Y, Zhang S Q, et al. Synthesis of low band gap polymer and its application in highly efficient polymer solar cells[J]. J Am Chem Soc, 2009, 131: 15 586-15 587.

[8] Hoven C V, Dang X D, Coffin R C, et al. Improved performance of polymer bulk heterojunction solar cells through the reduction of phase separation via solvent additives[J]. Adv Mater, 2010, 22: E63-E66.

[9] Zhang Y, Hau S K, Yip H, et al. Efficient polymer solar cells based on the copolymersof benzodithiophene and thienopyrroledione[J]. Chem Mater, 2010, 22(9): 2 696-2 698.

[10] Li Y W, Chen Y J, Liu X, et al. Controlling blend film morphology by varying alkyl side chain in highly coplanar donor_acceptor copolymers for photovoltaic application[J]. Macromolecules, 2011, 44: 6 370-6 381.

[11] Wang M, Hu X W, Liu P, et al. Donor_acceptor conjugated polymer based on naphtho [1,2-c∶5,6-c] bis [1,2,5] thiadiazole for high-performance polymer solar cells[J]. J Am Chem Soc, 2011, 133: 9 638-9 641.

[12] Liang Y Y, Xu Z, Xia J B, et al. For the bright future-bulk heterojunction polymer solar cells with power conversion efficiency of 7.4%[J]. Adv Mater, 2010, 22(20): E135-138.

[13] Liang Y Y, Feng D Q, Wu Y, et al. Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties[J]. J Am Chem Soc, 2009, 131: 7 792-7 799.

[14] Zhao Yu-mei(赵玉梅), Liu Li-jun(刘力军), Miao Zhen-chun(缪振春). Structral determination of an aglycome by long-range DEPT and selective NOESY techniques(选择性远程DEPT和选择性NOESY技术用于苷类化合物的结构研究)[J]. Chinese J Magn Reson(波谱学杂志), 2008, 25(3): 342-348.

[15] Zhao Yu-mei(赵玉梅), Tang Li-he(汤立合), Miao Zhen-chun(缪振春), et al. NMR and stereochemistry studies of fexofenadine hydrochloride(盐酸非索那定的NMR归属和立体化学研究)[J]. Chinese J Magn Reson(波谱学杂志), 2011, 28(2): 265-271.

[16] Yang Zhen-yun(杨振云), Wang Shi-hua(王世华), Liu Xiu-mei(刘秀梅), et al. The NMR studies of some butyl heterocyclic stannic compounds(杂环基丁基锡化合物的NMR研究)[J]. J Instrum Anal(分析测试学报), 1994, 13(1): 15-19.

[17] Yang Zhen-yun(杨振云), Wang Shi-hua(王世华), Liu Xiu-mei(刘秀梅), et al. The ¹³C NMR studies of alkyl, phenyl and five-membered heteroring tin compound(苯基五元杂环基锡化合物的NMR研究)[J]. Chinese J Magn Reson(波谱学杂志), 1989, 6(4): 489-493.

[18] Chen Mu-zi(陈木子), Wang Lu(王璐), Zhang Hai-lu(张海禄), et al. NMR analysis of targeted drug gefitinib(靶向新药吉非替尼的核磁共振波谱研究)[J]. Chinese J Magn Reson(波谱学杂志), 2011, 28(3): 413-418.

[19] Cao Xue(曹雪), Li Yue-qing(李悦青), Liu Ji-hong(刘季红), et al. NMR characterization of a novel curcumol derivative(一种新型的莪术醇衍生物的波谱学分析)[J]. Chinese J Magn Reson(波谱学杂志), 2011, 28(3): 399-406