Prevalent intrinsic emission from nonaromatic amino acids and poly(amino acids)

Xiaohong Chen1, Weijian Luo1, Huili Ma2, Qian Peng3, Wang Zhang Yuan1, Yongming Zhang1
1School of Chemistry and Chemical Engineering, Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Shanghai Electrochemical Energy Devices Research Center, Shanghai Jiao Tong University, Shanghai, China
2Department of Chemistry, Tsinghua University, Beijing, China
3Institute of Chemistry, Chinese Academy of Sciences, Beijing, China

Tóm tắt

Từ khóa


Tài liệu tham khảo

Saviotti ML, Galley WC. Proc Natl Acad Sci USA, 1974, 71: 4154–4158

Vanderkooi JM, Calhoun DB, Englander SW. Science, 1987, 236: 568–569

Papp S, Vanderkooi JM. Photochem Photobiol, 1989, 49: 775–784

Lakowicz JR. Principles of Fluorescence Spectroscopy. 3rd Ed. New York: Springer, 2006

Maki AH, Zuclich J. Top Curr Chem, 1975, 54: 115–163

Homchaudhuri L, Swaminathan R. Chem Lett, 2001, 30: 844–845

Homchaudhuri L, Swaminathan R. Bull Chem Soc Jpn, 2004, 77: 765–769

Shukla A, Mukherjee S, Sharma S, Agrawal V, Radha Kishan KV, Guptasarma P. Archives Biochem Biophys, 2004, 428: 144–153

Chan FTS, Kaminski Schierle GS, Kumita JR, Bertoncini CW, Dobson CM, Kaminski CF. Analyst, 2013, 138: 2156–2162

Pinotsi D, Grisanti L, Mahou P, Gebauer R, Kaminski CF, Hassanali A, Kaminski Schierle GS. J Am Chem Soc, 2016, 138: 3046–3057

Sharpe S, Simonetti K, Yau J, Walsh P. Biomacromolecules, 2011, 12: 1546–1555

Del Mercato LL, Pompa PP, Maruccio G, Della Torre A, Sabella S, Tamburro AM, Cingolani R, Rinaldi R. Proc Natl Acad Sci USA, 2007, 104: 18019–18024

Pinotsi D, Buell AK, Dobson CM, Kaminski Schierle GS, Kaminski CF. ChemBioChem, 2013, 14: 846–850

Ye R, Liu Y, Zhang H, Su H, Zhang Y, Xu L, Hu R, Kwok RTK, Wong KS, Lam JWY, Goddard WA, Tang BZ. Polym Chem, 2017, 8: 1722–1727

Gong YY, Tan YQ, Mei J, Zhang YR, Yuan WZ, Zhang YM, Sun JZ, Tang BZ. Sci China Chem, 2013, 56: 1178–1182

Zhou Q, Cao B, Zhu C, Xu S, Gong Y, Yuan WZ, Zhang Y. Small, 2016, 12: 6586–6592

Yuan WZ, Zhang Y. J Polym Sci Part A-Polym Chem, 2017, 55: 560–574

Lee WI, Bae Y, Bard AJ. J Am Chem Soc, 2004, 126: 8358–8359

Wang D, Imae T. J Am Chem Soc, 2004, 126: 13204–13205

Zhu S, Song Y, Shao J, Zhao X, Yang B. Angew Chem Int Ed, 2015, 54: 14626–14637

Sun M, Hong CY, Pan CY. J Am Chem Soc, 2012, 134: 20581–20584

Pucci A, Rausa R, Ciardelli F. Macromol Chem Phys, 2008, 209: 900–906

Zhao E, Lam JWY, Meng L, Hong Y, Deng H, Bai G, Huang X, Hao J, Tang BZ. Macromolecules, 2015, 48: 64–71

Miao X, Liu T, Zhang C, Geng X, Meng Y, Li X. Phys Chem Chem Phys, 2016, 18: 4295–4299

Yu W, Wu Y, Chen J, Duan X, Jiang XF, Qiu X, Li Y. RSC Adv, 2016, 6: 51257–51263

Niu S, Yan H, Chen Z, Li S, Xu P, Zhi X. Polym Chem, 2016, 7: 3747–3755

All experiments were conducted at room temperature unless specified. Though some concentrated nonaromatic amino acids are nonemissive at room temperature, they do become emissive when frozen by liquid nitrogen (Figure S1). And some relatively weakly emissive crystals (i.e. L-Leu, D-Leu, and D-Met) get more emissive upon cooling to 77 K (Figure S7)

Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ. Chem Rev, 2015, 115: 11718–11940

Fan Z, Sun L, Huang Y, Wang Y, Zhang M. Nat Nanotech, 2016, 11: 388–394

Tested with the detector at nanosecond scale

For the Perkin Elmer LS 55 fluorescence spectrometer, with a t d≥0.1 ms, all prompt fluorescence signals with nanoscale lifetime can be excluded

Yuan WZ, Shen XY, Zhao H, Lam JWY, Tang L, Lu P, Wang C, Liu Y, Wang Z, Zheng Q, Sun JZ, Ma Y, Tang BZ. J Phys Chem C, 2010, 114: 6090–6099

Wang CR, Gong YY, Yuan WZ, Zhang YM. Chin Chem Lett, 2016, 27: 1184–1192

Hirata S, Totani K, Zhang J, Yamashita T, Kaji H, Marder SR, Watanabe T, Adachi C. Adv Funct Mater, 2013, 23: 3386–3397

An Z, Zheng C, Tao Y, Chen R, Shi H, Chen T, Wang Z, Li H, Deng R, Liu X, Huang W. Nat Mater, 2015, 14: 685–690

Yang Z, Mao Z, Zhang X, Ou D, Mu Y, Zhang Y, Zhao C, Liu S, Chi Z, Xu J, Wu YC, Lu PY, Lien A, Bryce MR. Angew Chem Int Ed, 2016, 55: 2181–2185

Gong Y, Chen G, Peng Q, Yuan WZ, Xie Y, Li S, Zhang Y, Tang BZ. Adv Mater, 2015, 27: 6195–6201

Li C, Tang X, Zhang L, Li C, Liu Z, Bo Z, Dong YQ, Tian YH, Dong Y, Tang BZ. Adv Opt Mater, 2015, 3: 1184–1190

Xu S, Chen R, Zheng C, Huang W. Adv Mater, 2016, 28: 9920–9940

Xie Y, Ge Y, Peng Q, Li C, Li Q, Li Z. Adv Mater, 2017, 29: 1606829

Zhao W, He Z, Lam JWY, Peng Q, Ma H, Shuai Z, Bai G, Hao J, Tang BZ. Chem, 2016, 1: 592–602

Wei J, Liang B, Duan R, Cheng Z, Li C, Zhou T, Yi Y, Wang Y. Angew Chem Int Ed, 2016, 55: 15589–15593

Yan D. Sci China Chem, 2017, 60: 163–164

He G, Torres Delgado W, Schatz DJ, Merten C, Mohammadpour A, Mayr L, Ferguson MJ, McDonald R, Brown A, Shankar K, Rivard E. Angew Chem Int Ed, 2014, 53: 4587–4591

Chen H, Yao X, Ma X, Tian H. Adv Opt Mater, 2016, 4: 1397–1401

Shimizu M, Kimura A, Sakaguchi H. Eur J Org Chem, 2016, 2016: 467–473

Chen X, Xu C, Wang T, Zhou C, Du J, Wang Z, Xu H, Xie T, Bi G, Jiang J, Zhang X, Demas JN, Trindle CO, Luo Y, Zhang G. Angew Chem Int Ed, 2016, 55: 9872–9876

Boldyreva EV, Kolesnik EN, Drebushchak TN, Ahsbahs H, Beukes JA, Weber H-P. Z Kristallogr, 2005, 220: 58–65

CCDC 1542778 contains the supplementary crystallographic data for L-Ile. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif

Previously, glutathione was reported to be nonluminescent (see Ref. [8]), our results, however, show it can be emissive under proper conditions. Detailed results will be reported later