Vinyl-functionalized multicolor benzothiadiazoles: design,synthesis, crystal structures and mechanically-responsive performance
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摘要
Benzothiadiazole(BTD) has been extensively used as a building block in optical materials. In this work, a class of π-conjugated BTD-based luminogens BTD-685, BTD-580, BTD-675 and BTD-565 were designed by varying donor units and facilely synthesized by Heck coupling reaction. It was found that their emission in solid state covered the regio from orange, red to near infrared fluorescence. Investigation on photo-physical property manifested that they had strong solvatochromic behavior except symmetric 2-vinylpyridine substituted BTD-565. Crystal X-ray diffraction analysis revealed that they involved in multi weak intermolecular interactions. And loose molecular packing implied that they can be easily rearranged under external force stimuli.Indeed, all compounds showed reversible mechanically-responsive behavior in solid state. Interestingly, the vinylpyridinecontaining BTD-565 exhibited hypochromatic mechanochromic behavior, whereas others showed bathochromic mechanochromism behavior. It was worth mentioning that BTD-675 had self-recovery behavior after grinding. The powder X-ray diffraction study showed that these chromic processes may be mainly attributed to the reversible morphological changes between crystalline and amorphous phase upon grinding or fuming. These observations suggested that the vinyl-functionalized benzothiadiazoles can be considered as a type of excellent candidates in mechanically-responsive chromic materials.
Benzothiadiazole(BTD) has been extensively used as a building block in optical materials. In this work, a class of π-conjugated BTD-based luminogens BTD-685, BTD-580, BTD-675 and BTD-565 were designed by varying donor units and facilely synthesized by Heck coupling reaction. It was found that their emission in solid state covered the regio from orange, red to near infrared fluorescence. Investigation on photo-physical property manifested that they had strong solvatochromic behavior except symmetric 2-vinylpyridine substituted BTD-565. Crystal X-ray diffraction analysis revealed that they involved in multi weak intermolecular interactions. And loose molecular packing implied that they can be easily rearranged under external force stimuli.Indeed, all compounds showed reversible mechanically-responsive behavior in solid state. Interestingly, the vinylpyridinecontaining BTD-565 exhibited hypochromatic mechanochromic behavior, whereas others showed bathochromic mechanochromism behavior. It was worth mentioning that BTD-675 had self-recovery behavior after grinding. The powder X-ray diffraction study showed that these chromic processes may be mainly attributed to the reversible morphological changes between crystalline and amorphous phase upon grinding or fuming. These observations suggested that the vinyl-functionalized benzothiadiazoles can be considered as a type of excellent candidates in mechanically-responsive chromic materials.
Benzothiadiazole(BTD) has been extensively used as a building block in optical materials. In this work, a class of π-conjugated BTD-based luminogens BTD-685, BTD-580, BTD-675 and BTD-565 were designed by varying donor units and facilely synthesized by Heck coupling reaction. It was found that their emission in solid state covered the regio from orange, red to near infrared fluorescence. Investigation on photo-physical property manifested that they had strong solvatochromic behavior except symmetric 2-vinylpyridine substituted BTD-565. Crystal X-ray diffraction analysis revealed that they involved in multi weak intermolecular interactions. And loose molecular packing implied that they can be easily rearranged under external force stimuli.Indeed, all compounds showed reversible mechanically-responsive behavior in solid state. Interestingly, the vinylpyridinecontaining BTD-565 exhibited hypochromatic mechanochromic behavior, whereas others showed bathochromic mechanochromism behavior. It was worth mentioning that BTD-675 had self-recovery behavior after grinding. The powder X-ray diffraction study showed that these chromic processes may be mainly attributed to the reversible morphological changes between crystalline and amorphous phase upon grinding or fuming. These observations suggested that the vinyl-functionalized benzothiadiazoles can be considered as a type of excellent candidates in mechanically-responsive chromic materials.
引文
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11 Chen J,Li D,Chi W,Liu G,Liu SH,Liu X,Zhang C,Yin J.Chem Eur J,2018,24:3671-3676
12 Xue P,Yao B,Sun J,Xu Q,Chen P,Zhang Z,Lu R.J Mater Chem C,2014,2:3942-3950
13 Zhu H,Huang J,Kong L,Tian Y,Yang J.Dyes Pigments,2018,151:140-148
14(a)Yan X,Cook TR,Wang P,Huang F,Stang PJ.Nat Chem,2015,7:342-348;(b)Qin A,Tang BZ.Sci China Chem,2018,61:879-881;(c)Ding S,Liu M,Hong Y.Sci China Chem,2018,61:882-891
15(a)Aldred MP,Zhang GF,Li C,Chen G,Chen T,Zhu MQ.J Mater Chem C,2013,1:6709-6718;(b)Gao P,Tsao HN,Teuscher J,Gr?tzel M.Chin Chem Lett,2018,29:289-292;(c)Jiang M,Gu X,Lam JWY,Zhang Y,Kwok RTK,Wong KS,Tang BZ.Chem Sci,2017,8:5440-5446
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17 Roy B,Reddy MC,Hazra P.Chem Sci,2018,9:3592-3606
18 Zhang X,Chi Z,Xu B,Chen C,Zhou X,Zhang Y,Liu S,Xu J.JMater Chem,2012,22:18505-18513
2(a)Xie Y,Li Z.Chem,2018,4:943-971;(b)Yan L,Zhang Y,Xu B,Tian W.Nanoscale,2016,8:2471-2487;(c)Huang X,Qian L,Zhou Y,Liu M,Cheng Y,Wu H.J Mater Chem C,2018,6:5075-5096;(d)Wang C,Li Z.Mater Chem Front,2017,1:2174-2194;(e)Teng XY,Wu XC,Cao YQ,Jin YH,Li Y,Yan XL,Wang BW,Chen LG.Chin Chem Lett,2017,28:1485-1491;(f)Xue P,Ding J,Wang P,Lu R.J Mater Chem C,2016,4:6688-6706;(g)Haidekker MA,Theodorakis EA.J Mater Chem C,2016,4:2707-2718;(h)Chen Z,Zhang J,Song M,Yin J,Yu GA,Liu SH.Chem Commun,2015,51:326-329;(i)Xue S,Qiu X,Sun Q,Yang W.J Mater Chem C,2016,4:1568-1578;(j)Chen W,Pan Y,Chen J,Ye F,Liu SH,Yin J.Chin Chem Lett,2018,29:1429-1435;(k)Chi Z,Zhang X,Xu B,Zhou X,Ma C,Zhang Y,Liu S,Xu J.Chem Soc Rev,2012,41:3878-3896;(l)Dou CD,Li D,Zhang HY,Gao HZ,Zhang JY,Wang Y.Sci China Chem,2011,54:641-650
3 Dong Y,Xu B,Zhang J,Tan X,Wang L,Chen J,Lv H,Wen S,Li B,Ye L,Zou B,Tian W.Angew Chem Int Ed,2012,51:10782-10785
4 Tanioka M,Kamino S,Muranaka A,Ooyama Y,Ota H,Shirasaki Y,Horigome J,Ueda M,Uchiyama M,Sawada D,Enomoto S.J Am Chem Soc,2015,137:6436-6439
5 Mao Z,Yang Z,Mu Y,Zhang Y,Wang YF,Chi Z,Lo CC,Liu S,Lien A,Xu J.Angew Chem Int Ed,2015,54:6270-6273
6 Yang J,Ren Z,Xie Z,Liu Y,Wang C,Xie Y,Peng Q,Xu B,Tian W,Zhang F,Chi Z,Li Q,Li Z.Angew Chem Int Ed,2017,56:880-884
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8(a)Chen PZ,Zhang H,Niu LY,Zhang Y,Chen YZ,Fu HB,Yang QZ.Adv Funct Mater,2017,27:1700332-1700341;(b)Suzuki T,Okada H,Nakagawa T,Komatsu K,Fujimoto C,Kagi H,Matsuo Y.Chem Sci,2018,9:475-482;(c)Zhang G,Lu J,Sabat M,Fraser CL.J Am Chem Soc,2010,132:2160-2162;(d)Nagura K,Saito S,Yusa H,Yamawaki H,Fujihisa H,Sato H,Shimoikeda Y,Yamaguchi S.J Am Chem Soc,2013,135:10322-10325;(e)Wang L,Wang K,Zou B,Ye K,Zhang H,Wang Y.Adv Mater,2015,27:2918-2922;(f)Yoon SJ,Chung JW,Gierschner J,Kim KS,Choi MG,Kim D,Park SY.J Am Chem Soc,2010,132:13675-13683;(g)Ma X,Hu L,Han X,Yin J.Chin Chem Lett,2018,29:1489-1492;(h)Sathyanarayana A,Nakamura S,Hisano K,Tsutsumi O,Srinivas K,Prabusankar G.Sci China Chem,2018,61:957-965
9(a)Jadhav T,Dhokale B,Patil Y,Mobin SM,Misra R.J Phys Chem C,2016,120:24030-24040;(b)Sun J,Dai Y,Ouyang M,Zhang Y,Zhan L,Zhang C.J Mater Chem C,2015,3:3356-3363;(c)Xue P,Ding J,Chen P,Wang P,Yao B,Sun J,Sun J,Lu R.J Mater Chem C,2016,4:5275-5280
10(a)Justin Thomas K,Lin J,Velusamy M,Tao YT,Chuen CH.Adv Funct Mater,2004,14:83-90;(b)Zhang M,Tsao HN,Pisula W,Yang C,Mishra AK,Müllen K.J Am Chem Soc,2007,129:3472-3473;(c)Jia B,Wu Y,Zhao F,Yan C,Zhu S,Cheng P,Mai J,Lau TK,Lu X,Su CJ,Wang C,Zhan X.Sci China Chem,2017,60:257-263
11 Chen J,Li D,Chi W,Liu G,Liu SH,Liu X,Zhang C,Yin J.Chem Eur J,2018,24:3671-3676
12 Xue P,Yao B,Sun J,Xu Q,Chen P,Zhang Z,Lu R.J Mater Chem C,2014,2:3942-3950
13 Zhu H,Huang J,Kong L,Tian Y,Yang J.Dyes Pigments,2018,151:140-148
14(a)Yan X,Cook TR,Wang P,Huang F,Stang PJ.Nat Chem,2015,7:342-348;(b)Qin A,Tang BZ.Sci China Chem,2018,61:879-881;(c)Ding S,Liu M,Hong Y.Sci China Chem,2018,61:882-891
15(a)Aldred MP,Zhang GF,Li C,Chen G,Chen T,Zhu MQ.J Mater Chem C,2013,1:6709-6718;(b)Gao P,Tsao HN,Teuscher J,Gr?tzel M.Chin Chem Lett,2018,29:289-292;(c)Jiang M,Gu X,Lam JWY,Zhang Y,Kwok RTK,Wong KS,Tang BZ.Chem Sci,2017,8:5440-5446
16 Krishna GR,Kiran MSRN,Fraser CL,Ramamurty U,Reddy CM.Adv Funct Mater,2013,23:1422-1430
17 Roy B,Reddy MC,Hazra P.Chem Sci,2018,9:3592-3606
18 Zhang X,Chi Z,Xu B,Chen C,Zhou X,Zhang Y,Liu S,Xu J.JMater Chem,2012,22:18505-18513