Top

Published in:

2024 | OriginalPaper | Chapter

4. Various Stacking Patterns of Two-Dimensional Molecular Assemblies in Hydrogen-Bonded Cocrystals: Insight into Competitive Intermolecular Interactions and Control of Stacking Patterns

Author : Dr. Masaki Donoshita

Published in: Design of Crystal Structures Using Hydrogen Bonds on Molecular-Layered Cocrystals and Proton–Electron Mixed Conductor

Publisher: Springer Nature Singapore

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

Control over stacking patterns in two-dimensional (2D) molecular assemblies is demonstrated by chemical modification. A target system is a hydrogen-bonded cocrystal (2:1) composed of 2-pyrrolidone (Py) and chloranilic acid (CA) (PyCA). X-ray crystallography revealed that weak intersheet interactions result in a variety of metastable overlapping patterns comprising 2D assemblies, mainly formed via hydrogen bonds, allowing reversible and irreversible structural phase transitions. Cocrystals of Py and anilic acids bearing different halogens were prepared, in which the 2D assemblies, isostructural to those observed in PyCA, exhibited various overlapping patterns. The order of stability for each overlapping pattern estimated using calculations of the intermolecular interactions did not completely coincide with those indicated by our experimental results. This can be explained by considering the entropic effect, that is, the molecular motion of Py, as detected using nuclear quadrupole resonance spectroscopy.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

previous chapter Drastic Rearrangement of Self-Assembled Hydrogen-Bonded Tapes in a Molecular Crystal

next chapter General Conclusion

Miller JS (ed) (1983) Extended linear chain compounds, vol 1, 2, 3. Plenum Press, New York

Grasso V (ed) (1986) Electronic structure and electronic transitions in layered materials. D. Reidel Publishing, Dordrecht

Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311–2327CrossRef

Moulton B, Zaworotko MJ (2001) Chem Rev 101:1629–1658PubMedCrossRef

Bernstein J (2020) Polymorphism in molecular crystals, 2nd edn. Oxford University Press, New YorkCrossRef

Israelachvili JN (2011) Intermolecular and surface forces, 3rd edn. Academic Press, New York

Nyman J, Day GM (2015) CrystEngComm 17:5154–5165CrossRef

Aakerçy CB, Fasulo M, Schultheiss N, Desper J, Moore C (2007) J Am Chem Soc 129:13772–13773CrossRef

Banerjee R, Mondal R, Howard JAK, Desiraju GR (2006) Cryst Growth Des 6:999–1009CrossRef

10.

Zerkowski JA, MacDonald JC, Seto CT, Wierda DA, Whitesides GM (1994) J Am Chem Soc 116:2382–2391CrossRef

11.

Palacin S, Chin DN, Simanek EE, MacDonald JC, Whitesides GM, McBride MT, Palmore GTR (1997) J Am Chem Soc 119:11807–11816CrossRef

12.

Chin DN, Palmore GTR, Whitesides GM (1999) J Am Chem Soc 121:2115–2122CrossRef

13.

Paine RT, Narula CK (1990) Chem Rev 90:73–91CrossRef

14.

Han GH, Duong DL, Keum DH, Yun SJ, Lee YH (2018) Chem Rev 118:6297–6336PubMedCrossRef

15.

Chakraborty G, Park IH, Medishetty R, Vittal JJ (2021) Chem Rev 121:3751–3891PubMedCrossRef

16.

Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV, Grigorieva IV, Firsov AA (2004) Science 306:666–669PubMedCrossRef

17.

Geng K, He T, Liu R, Dalapati S, Tan KT, Li Z, Tao S, Gong Y, Jiang Q, Jiang D (2020) Chem Rev 120:8814–8933PubMedCrossRef

18.

Naik I, Rastogi AK (2011) Pramana 76:957–963CrossRef

19.

Cao Y, Fatemi V, Fang S, Watanabe K, Taniguchi T, Kaxiras E, Jarillo-Herrero P (2018) Nature 556:43–50PubMedCrossRef

20.

Cao Y, Fatemi V, Demir A, Fang S, Tomarken SL, Luo JY, Sanchez-Yamagishi JD, Watanabe K, Taniguchi T, Kaxiras E, Ashoori RC, Jarillo-Herrero P (2018) Nature 556:80–84

21.

Huskić I, Novendra N, Lim DW, Topić F, Titi HM, Pekov IV, Krivovichev SV, Navrotsky A, Kitagawa H, Friščić T (2019) Chem Sci 10:4923–4929PubMedPubMedCentralCrossRef

22.

Tang WQ, Zhao YJ, Xu M, Xu JY, Meng SS, Yin YD, Zhang QH, Gu L, Liu DH, Gu ZY (2021) Angew Chem Int Ed 60:6920–6925CrossRef

23.

Davey RJ, Maginn SJ, Andrews SJ, Black SN, Buckley AM, Cottier D, Dempsey P, Plowman R, Rout JE, Stanley DR, Taylor A (1994) J Chem Soc Faraday Trans 90:1003–1009CrossRef

24.

Karothu DP, Weston J, Desta IT, Naumov P (2016) J Am Chem Soc 138:13298–13306PubMedCrossRef

25.

Sasaki T, Miyamoto Y, Takamizawa S (2020) Cryst Growth Des 20:4779–4782CrossRef

26.

Hunter CA, Sanders JKM (1990) J Am Chem Soc 112:5525–5534CrossRef

27.

Thakuria R, Nath NK, Saha BK (2019) Cryst Growth Des 19:523–528CrossRef

28.

Mooibroek TJ, Gamez P, Reedijk J (2008) CrystEngComm 10:1501–1515CrossRef

29.

Nishio M (2004) CrystEngComm 6:130–158CrossRef

30.

Grabowski SJ (2006) In: Hydrogen bonding-new insights. Springer, Dordrecht

31.

Maréchal Y (2007) In: The hydrogen bond and the water molecule: the physics and chemistry of water, aqueous and bio media, Elsevier, Amsterdam

32.

Steiner T (2002) Angew Chem Int Ed 41:48–76CrossRef

33.

MacDonald JC, Whitesides GM (1994) Chem Rev 94:2383–2420CrossRef

34.

Williams LJ, Jagadish B, Lyon SR, Kloster RA, Carducci MD, Mash EA (1999) Tetrahedron 55:14281–14300CrossRef

35.

Williams LJ, Jagadish B, Lansdown MG, Carducci MD, Mash EA (1999) Tetrahedron 55:14301–14322CrossRef

36.

Takasawa R, Yoshikawa I, Araki K (2004) Org Biomol Chem 2:1125–1132PubMedCrossRef

37.

Sada K, Inoue K, Tanaka T, Tanaka A, Epergyes A, Nagahama S, Matsumoto A, Miyata M (2004) J Am Chem Soc 126:1764–1771PubMedCrossRef

38.

Gong B, Zheng C, Skrzypczak-Jankun E, Yan Y, Zhang J (1998) J Am Chem Soc 120:11194–11195CrossRef

39.

Gong B, Zheng C, Zeng H, Zhu J (1999) J Am Chem Soc 121:9766–9767CrossRef

40.

Zerkowski JA, Seto CT, Wierda DA, Whitesides GM (1990) J Am Chem Soc 112:9025–9026CrossRef

41.

Zerkowski JA, Seto CT, Whitesides GM (1992) J Am Chem Soc 114:5473–5475CrossRef

42.

Zerkowski JA, Whitesides GM (1994) J Am Chem Soc 116:4298–4304CrossRef

43.

Zerkowski JA, Mathias JP, Whitesides GM (1994) J Am Chem Soc 116:4305–4315CrossRef

44.

Russell VA, Etter MC, Ward MD (1994) J Am Chem Soc 116:1941–1952CrossRef

45.

Russell VA, Evans CC, Li W, Ward MD (1997) Science 276:575–579PubMedCrossRef

46.

Ermer O (1988) J Am Chem Soc 110:3747–3754CrossRef

47.

Gotoh K, Ishida H (2011) Acta Crystallogr Sect C 67:o500–o504CrossRef

48.

Donoshita M, Hayashi M, Ikeda R, Yoshida Y, Morikawa S, Sugimoto K, Kitagawa H (2018) Chem Commun 54:8571–8574CrossRef

49.

Akutagawa T, Koshinaka H, Sato D, Takeda S, Noro S, Takahashi H, Kumai R, Tokura Y, Nakamura T (2009) Nat Mater 8:342–347PubMedCrossRef

50.

Hayami S, Murata K, Urakami D, Kojima Y, Akita M, Inoue K (2008) Chem Commun 6510–6512

51.

Su X, Zuo F, Schlueter JA, Kelly ME, Williams JM (1998) Phys Rev B 57:R14056–R14059CrossRef

52.

Torrey HA, Hunter WH (1912) J Am Chem Soc 34:702–716CrossRef

53.

Murase R, Abrahams BF, D’Alessandro DM, Davies CG, Hudson TA, Jameson GNL, Moubaraki B, Murray KS, Robson R, Sutton AL (2017) Inorg Chem 56:9025–9035PubMedCrossRef

54.

Sheldrick GM (2014) SHELXT Version 2014/5. Acta Cryst A70:C1437

55.

Sheldrick GM (2014) SHELXL Version 2014/3. Acta Cryst A64:112–122

56.

CrystalStructure (2018) Version 4.3, Rigaku Corporation, Tokyo, Japan

57.

Gaussian 09, Revision A.02, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Gaussian Inc., Wallingford, CT

58.

Psi4 v1.3.2, Parrish RM, Burns LA, Smith DGA, Simmonett AC, DePrince III AE, Hohenstein EG, Bozkaya U, Sokolov AY, Di Remigio R, Richard RM, Gonthier JF, James AM, McAlexander HR, Kumar A, Saitow M, Wang X, Pritchard BP, Verma P, Schaefer III HF, Patkowski K, King RA, Valeev EF, Evangelista FA, Turney JM, Crawford TD, Sherrill CD (2017) J Chem Theory Comput 13:3185–3197

59.

Jeziorski B, Moszynski R, Szalewicz K (1994) Chem Rev 94:1887–1930CrossRef

60.

Parker TM, Burns LA, Parrish RM, Ryno AG, Sherrill CD (2014) J Chem Phys 140:094106PubMedCrossRef

61.

Bondi A (1964) J Phys Chem 68:441–451CrossRef

62.

Wang H, Wang W, Jin WJ (2016) Chem Rev 116:5072–5104PubMedCrossRef

63.

Politzer P, Murray JS (2018) J Comput Chem 39:464–471PubMedCrossRef

64.

Gavezzotti A (2002) J Phys Chem B 106:4145–4154CrossRef

65.

Miller TM (2019) Polarizabilities of atoms and molecules. In: Rumble JR (ed) CRC handbook of chemistry and physics, 100th ed. CRC Press, Boca Raton, FL, pp 10–96–10–97

66.

In the temperature region above 298 K, we used samples sealed in glass capillaries

67.

Zhuo M-P, Tao Y-C, Wang X-D, Wu Y, Chen S, Liao L-S, Jiang L (2018) Angew Chem Int Ed 57:11300–11304CrossRef

68.

Liu Y, Hu H, Xu L, Qiu B, Liang J, Ding F, Wang K, Chu M, Zhang W, Ma M, Chen B, Yang X, Zhao YS (2020) Angew Chem Int Ed 59:4456–4463CrossRef

69.

Das TP, Hahn EL (1958) Nuclear quadrupole resonance spectroscopy. In: Solid state physics (Suppl. 1), Academic Press, New York

70.

Rigamonti A (1984) Adv Phys 33:115–191CrossRef

71.

Tobu Y, Ikeda R, Nihei TA, Gotoh K, Ishida H, Asaji T (2012) Phys Chem Chem Phys 14:12347–12354PubMedCrossRef

72.

Nogaj B (1988) Bull Chem Soc Jpn 61:549–556CrossRef

73.

Woessner DE, Gutowsky HS (1963) J Chem Phys 39:440–456CrossRef

74.

Horiuchi S, Ishibashi S (2020) J Phys Soc Jpn 89:051009CrossRef

75.

Davydov AS (1991) In: Solitons in molecular systems, 2nd ed. Kluwer Academic Publishers, Dordrecht, (English translation)

76.

Takasu I, Sugawara T, Mochida T (2004) J Phys Chem B 108:18495–18499CrossRef

77.

Allen FH, Watson DG, Brammer A, Orpen AG, Taylor R (1999) Typical interatomic distances: organic compounds. In: Prince E (ed) International tables for crystallography volume C: Mathematical, physical and chemical tables, 2nd ed. Kluwer Academic Publishers, Dordrecht, pp 782–803

78.

Donoshita M, Yoshida Y, Hayashi M, Ikeda R, Tanaka S, Yamamura Y, Saito K, Kawaguchi S, Sugimoto K, Kitagawa H (2021) Angew Chem Int Ed 60:22839–22848CrossRef

Title: Various Stacking Patterns of Two-Dimensional Molecular Assemblies in Hydrogen-Bonded Cocrystals: Insight into Competitive Intermolecular Interactions and Control of Stacking Patterns
Author: Dr. Masaki Donoshita
Publisher: Springer Nature Singapore
Book: Design of Crystal Structures Using Hydrogen Bonds on Molecular-Layered Cocrystals and Proton–Electron Mixed Conductor
Print ISBN: 978-981-9970-61-2

Electronic ISBN: 978-981-9970-62-9

Copyright Year: 2024
DOI: https://doi.org/10.1007/978-981-99-7062-9_4