Crystal Violet Lactone Salicylaldehyde Hydrazone Zn(II) Complex: a Reversible Photochromic Material Both in Solution and in Solid Matrix

Overview

Journal Sci Rep

Specialty Science

Date 2015 Sep 29

PMID 26412101

Citations 1

Authors

Kai Li

Yuanyuan Li

Jing Tao

Lu Liu

Lili Wang

Hongwei Hou

Aijun Tong

Affiliations

Soon will be listed here.

Abstract

Crystal violet lactone (CVL) is a classic halochromic dye which has been widely used as chromogenic reagent in thermochromic and piezochromic systems. In this work, a very first example of CVL-based reversible photochromic compound was developed, which showed distinct color change upon UV-visible light irradiation both in solution and in solid matrix. Moreover, metal complex of CVL salicylaldehyde hydrozone was facilely synthesized, exhibiting reversible photochromic properties with good fatigue resistance. It was served as promising solid material for photo-patterning.

Citing Articles

On-demand regulation of photochromic behavior through various counterions for high-level security printing.

Ma Y, Yu Y, She P, Lu J, Liu S, Huang W Sci Adv. 2020; 6(16):eaaz2386.

PMID: 32494612 PMC: 7164943. DOI: 10.1126/sciadv.aaz2386.

References

Chen X, Pradhan T, Wang F, Kim J, Yoon J . Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. Chem Rev. 2011; 112(3):1910-56. DOI: 10.1021/cr200201z. View

Cui X, Zhao J, Zhou Y, Ma J, Zhao Y . Reversible photoswitching of triplet-triplet annihilation upconversion using dithienylethene photochromic switches. J Am Chem Soc. 2014; 136(26):9256-9. DOI: 10.1021/ja504211y. View

Chen Z, Zhou L, Bing W, Zhang Z, Li Z, Ren J . Light controlled reversible inversion of nanophosphor-stabilized Pickering emulsions for biphasic enantioselective biocatalysis. J Am Chem Soc. 2014; 136(20):7498-504. DOI: 10.1021/ja503123m. View

Xie X, Bakker E . Photoelectric conversion based on proton-coupled electron transfer reactions. J Am Chem Soc. 2014; 136(22):7857-60. DOI: 10.1021/ja503491k. View

Yamazoe S, Liu Q, McQuade L, Deiters A, Chen J . Sequential gene silencing using wavelength-selective caged morpholino oligonucleotides. Angew Chem Int Ed Engl. 2014; 53(38):10114-8. PMC: 4206551. DOI: 10.1002/anie.201405355. View

Nachtigall O, Kordel C, Urner L, Haag R . Photoresponsive switches at surfaces based on supramolecular functionalization with azobenzene-oligoglycerol conjugates. Angew Chem Int Ed Engl. 2014; 53(36):9669-73. DOI: 10.1002/anie.201403331. View

Belov V, Bossi M, Folling J, Boyarskiy V, Hell S . Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy. Chemistry. 2009; 15(41):10762-76. DOI: 10.1002/chem.200901333. View

Moorthy J, Mandal S, Mukhopadhyay A, Samanta S . Helicity as a steric force: stabilization and helicity-dependent reversion of colored o-quinonoid intermediates of helical chromenes. J Am Chem Soc. 2013; 135(18):6872-84. DOI: 10.1021/ja312027c. View

Li K, Xiang Y, Wang X, Li J, Hu R, Tong A . Reversible photochromic system based on rhodamine B salicylaldehyde hydrazone metal complex. J Am Chem Soc. 2014; 136(4):1643-9. DOI: 10.1021/ja411689w. View

10.

Wu L, Dai Y, Marriott G . Optical control of calcium affinity in a spiroamido-rhodamine based calcium chelator. Org Lett. 2011; 13(8):2018-21. PMC: 3147027. DOI: 10.1021/ol200408j. View

11.

Yang Y, Hughes R, Aprahamian I . Near-infrared light activated azo-BF2 switches. J Am Chem Soc. 2014; 136(38):13190-3. DOI: 10.1021/ja508125n. View

12.

Nakai H, Kitagawa K, Nakamori H, Tokunaga T, Matsumoto T, Nozaki K . Reversible switching of the luminescence of a photoresponsive gadolinium(III) complex. Angew Chem Int Ed Engl. 2013; 52(33):8722-5. DOI: 10.1002/anie.201303137. View

13.

Folling J, Belov V, Kunetsky R, Medda R, Schonle A, Egner A . Photochromic rhodamines provide nanoscopy with optical sectioning. Angew Chem Int Ed Engl. 2007; 46(33):6266-70. DOI: 10.1002/anie.200702167. View

14.

Kishida M, Kusamoto T, Nishihara H . Photoelectric signal conversion by combination of electron-transfer chain catalytic isomerization and photoisomerization on benzodimethyldihydropyrenes. J Am Chem Soc. 2014; 136(13):4809-12. DOI: 10.1021/ja412528d. View

15.

Li W, Li X, Xie Y, Wu Y, Li M, Wu X . Enantiospecific photoresponse of sterically hindered diarylethenes for chiroptical switches and photomemories. Sci Rep. 2015; 5:9186. PMC: 4361853. DOI: 10.1038/srep09186. View

16.

Yang Y, Hughes R, Aprahamian I . Visible light switching of a BF2-coordinated azo compound. J Am Chem Soc. 2012; 134(37):15221-4. DOI: 10.1021/ja306030d. View

17.

Iida A, Saito S, Sasamori T, Yamaguchi S . Borylated dibenzoborepin: synthesis by skeletal rearrangement and photochromism based on bora-Nazarov cyclization. Angew Chem Int Ed Engl. 2013; 52(13):3760-4. DOI: 10.1002/anie.201210236. View

18.

Best Q, Xu R, McCarroll M, Wang L, Dyer D . Design and investigation of a series of rhodamine-based fluorescent probes for optical measurements of pH. Org Lett. 2010; 12(14):3219-21. PMC: 2925113. DOI: 10.1021/ol1011967. View

19.

Hadjoudis E, Mavridis I . Photochromism and thermochromism of Schiff bases in the solid state: structural aspects. Chem Soc Rev. 2004; 33(9):579-88. DOI: 10.1039/b303644h. View

20.

Wu Y, Xie Y, Zhang Q, Tian H, Zhu W, Li A . Quantitative photoswitching in bis(dithiazole)ethene enables modulation of light for encoding optical signals. Angew Chem Int Ed Engl. 2014; 53(8):2090-4. DOI: 10.1002/anie.201309915. View