CuAAC Synthesis of Tetragonal Building Blocks Decorated with Nucleobases

Lidia Pop; Mirabela Ligia Golban; Niculina D. Hădade; Crina Socaci; Ion Grosu

doi:10.1055/s-0034-1378782

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(18): 2799-2804
DOI: 10.1055/s-0034-1378782

special topic

CuAAC Synthesis of Tetragonal Building Blocks Decorated with Nucleobases

Lidia Pop

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania

,

Mirabela Ligia Golban

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania

,

Niculina D. Hădade

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania

,

Crina Socaci

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania

^bNational Institute of Research and Development for Isotopic and Molecular Technologies (INCDTIM), Cluj-Napoca, 65-103 Donath Str., 400293 Cluj-Napoca, Romania eMail: igrosu@chem.ubbcluj.ro

,

Ion Grosu*

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania

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Abstract

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Abstract

The CuAAC synthesis and the characterization of new rigid nucleobase-decorated tetrapodands exhibiting 1,3,5,7-tetraphenyladamantane and 9,9′-spirobifluorene central units are reported. 1,3,5,7-Tetraphenyladamantane and 3,3′,6,6′-tetrasubstituted 9,9′-spirobifluorene derivatives are tetrahedral building blocks, while the derivatives of 2,2′,7,7′-tetrasubstituted 9,9′-spirobifluorene can lead to 2D architectures.

Key words

‘click’ chemistry - nucleobase-decorated building blocks - tetrapodands - tetraphenyladamantane - 9,9′-spirobifluorene

Volltext

Referenzen

References

1a Li M, Li D, O’Keeffe M, Yaghi OM. Chem. Rev. 2014; 114: 1343
1b O’Keeffe M, Yaghi OM. Chem. Rev. 2012; 112: 675
1c Schoedel A, Cairns AJ, Belmabkhout Y, Wojtas L, Mohamed M, Zhang Z, Proserpio DM, Eddaoudi M, Zaworotko MJ. Angew. Chem. Int. Ed. 2013; 52: 2902
1d Paz FA. A, Klinowski J, Vilela SM. F, Tomé JP. C, Cavaleiro JA. S, Rocha J. Chem. Soc. Rev. 2012; 41: 1088
1e Cook TR, Zheng Y.-R, Stang PJ. Chem Rev. 2013; 113: 734

2 Guillerm V, Kim D, Eubank JF, Luebke R, Liu X, Adil K, Lah MS, Eddaoudi M. Chem. Soc. Rev. 2014; 43: 6141

3a Ding S.-Y, Wang W. Chem. Soc. Rev. 2013; 42: 548
3b Addicoat MA, Tsotsalas M. Front. Mater. Sci. 2015; 2: 1
3c Feng X, Ding X, Jiang D. Chem. Soc. Rev. 2012; 41: 6010

4 Muller T, Bräse S. RSC Adv. 2014; 4: 6886

5a Yuan D, Lu W, Zhao D, Zhou H.-C. Adv. Mater. 2011; 23: 3723
5b Chun J, Kang S, Park N, Park EJ, Jin X, Kim K.-D, Seo HO, Lee SM, Kim HJ, Kwon WH, Park Y.-K, Kim JM, Kim YD, Son SU. J. Am. Chem. Soc. 2014; 136: 6786
5c Beaudoin D, Maris T, Wuest JD. Nat. Chem. 2013; 5: 830

6a Yu H, Shen C, Tian M, Qu J, Wang Z. Macromolecules 2012; 45: 5140
6b Zhang M, Chenab Y.-P, Zhou H.-C. CrystEngComm 2013; 15: 9544
6c Davies RP, Less R, Lickiss PD, Robertson K, White AJ. P. Cryst. Growth Des. 2010; 10: 4571
6d Davies RP, Less RJ, Lickiss PD, Robertson K, White AJ. P. Inorg. Chem. 2008; 47: 9958
6e Davies RP, Lickiss PD, Robertson K, White AJ. P. Aust. J. Chem. 2011; 64: 1239

7a Boldog I, Domasevitch KV, Baburin IA, Ott H, Gil-Hernandez B, Sanchiz J, Janiak C. CrystEngComm 2013; 15: 1235
7b Shen C, Bao Y, Wang Z. Chem. Commun. 2013; 49: 3321
7c Bhunia A, Boldog I, Moller A, Janiak C. J. Mater. Chem. A 2013; 1: 14990

8 Fournier J.-H, Maris T, Wuest JD. J. Org. Chem. 2004; 69: 1762

9a Kim J, Chen B, Reineke TM, Li H, Eddaoudi M, Moler DB, O’Keeffe M, Yaghi OM. J. Am. Chem. Soc. 2001; 123: 8239
9b Ma L, Jin A, Xie Z, Lin W. Angew. Chem. Int. Ed. 2009; 48: 9905
9c Wen L, Cheng P, Lin W. Chem. Commun. 2012; 48: 2846

10a He Y, Xiang S, Chen B. J. Am. Chem. Soc. 2011; 133: 14570
10b Boils D, Perron M.-E, Monchamp F, Duval H, Maris T, Wuest JD. Macromolecules 2004; 37: 7351
10c Fournier J.-H, Maris T, Wuest JD, Guo W, Galoppini E. J. Am. Chem. Soc. 2002; 125: 1002
10d Laliberté D, Maris T, Wuest JD. Can. J. Chem. 2004; 82: 386

11a Uribe-Romo FJ, Hunt JR, Furukawa H, Klock C, O’Keeffe M, Yaghi OM. J. Am. Chem. Soc. 2009; 131: 4570
11b El-Kaderi HM, Hunt JR, Mendoza-Cortes JL, Côté AP, Taylor RE, O’Keeffe M, Yaghi OM. Science 2007; 316: 268
11c Hunt JR, Doonan CJ, LeVangie JD, Côté AP, Yaghi OM. J. Am. Chem. Soc. 2008; 130: 11872

12a Ben T, Ren H, Ma SQ, Cao DP, Lan JH, Jing XF, Wang WC, Xu J, Deng F, Simmons JM, Qiu SL, Zhu GS. Angew. Chem. Int. Ed. 2009; 48: 9457
12b Lu W, Yuan D, Zhao D, Schilling CI, Plietzsch O, Muller T, Bräse S, Guenther J, Blüme J, Krishna R, Li Z, Zhou HC. Chem. Mater. 2010; 22: 5964
12c Schmidt J, Werner M, Thomas A. Macromolecules 2009; 42: 4426

13 Imaz I, Rubio-Martínez M, An J, Solé-Font I, Rosi NL, Maspoch D. Chem. Commun. 2011; 47: 7287

14a Beobide G, Castillo O, Luque A, Pérez-Yáñez S. CrystEngComm 2015; 17: 3051
14b Thomas-Gipson J, Pérez-Aguirre R, Beobide G, Castillo O, Luque A, Pérez-Yáñez S, Román P. Cryst. Growth Des. 2015; 15: 975

15 Amo-Ochoa P, Zamora F. Coord. Chem. Rev. 2014; 276: 34 ; and references cited therein

16a Plietzsch O, Schilling CI, Tolev M, Nieger M, Richert C, Muller T, Bräse S. Org. Biomol. Chem. 2009; 7: 4734
16b Singh A, Tolev M, Schilling CI, Bräse S, Griesser H, Richert C. J. Org. Chem. 2012; 77: 2718
16c Singh A, Tolev M, Meng M, Klenin K, Plietzsch O, Schilling CI, Muller T, Nieger M, Bräse S, Wenzel W, Richert C. Angew. Chem. Int. Ed. 2011; 50: 3227

17 Lu W, Yuan D, Zhao D, Schilling CI, Plietzsch O, Muller T, Bräse S, Guenther J, Blümel J, Krishna R, Li Z, Zhou H.-C. Chem. Mater. 2010; 22: 5964
18 Ren H, Tao Q, Gao Z, Liu D. Dyes Pigments 2012; 94: 136
19 Pop L, Dumitru F, Hădade ND, van der Lee A, Barboiu M, Grosu I. Org. Lett. 2015; 17: 3494
20 Golban ML, Paşcanu V, Hădade ND, Pop L, Socaci C, Grosu I. Synthesis 2014; 46: 1229

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