The design of organic structures in the solid state: hydrogen-bonded molecular "tapes"

Zerkowski, Jonathan A.; Seto, Christopher T.; Wierda, Derk A.; Whitesides, George M.

doi:10.1021/ja00180a083

Cited by 239 publications

(97 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2). 11,[101][102][103][104][105] Ironically the focus of these studies was not so much the physical properties of the resulting co-crystals but rather the supramolecular functionality of barbitals 106 and their complementarity with melamine. Nevertheless, these studies illustrated very well the potential diversity of forms that can exist for a particular API as more than 60 co-crystals were structurally characterized in this series of studies.…”

Section: Case Studies Of Pharmaceutical Co-crystalsmentioning

confidence: 99%

Pharmaceutical Co-Crystals

Vishweshwar

McMahon

Bis

et al. 2006

Journal of Pharmaceutical Sciences

893

634

View full text Add to dashboard Cite

Section: Case Studies Of Pharmaceutical Co-crystalsmentioning

confidence: 99%

Pharmaceutical Co-Crystals

Vishweshwar

McMahon

Bis

et al. 2006

Journal of Pharmaceutical Sciences

893

634

View full text Add to dashboard Cite

“…It was found that barbiturates or cyanurates could self-assemble into highly organized structures such as linear tapes, crinkle tapes, or rosettes with complementary hydrogen-bonding melamines in the solid state or solution. [10][11][12][13][14][15][16][17][18] More recently, the formation of hydrogenbonding networks between these complementary components has also been investigated in 2-D at the air-water interface. 19,20 Traditionally, it was believed that hydrogen bonding directed molecular recognition is difficult in polar media, such as water, due to the competition from the latter.…”

Section: Introductionmentioning

confidence: 99%

Polarization-Modulated Infrared Reflection Absorption Spectroscopic Studies of a Hydrogen-Bonding Network at the Air−Water Interface

et al. 1999

View full text Add to dashboard Cite

The hydrogen-bonding network formed between a triaminotriazine amphiphile (2C 18 TAZ, 1) and complementary barbituric acid (BA, 2) at the air-water interface is investigated by polarization-modulated infrared reflection absorption spectroscopy (PM-IRRAS). The molecular structure and orientation of the 1:1 hydrogenbonding network at the air-water interface is revealed in this study. Without the addition of BA to the subphase, the NH 2 scissoring of 2C 18 TAZ appeared in the spectrum as a broad negative absorption band between 1660 and 1605 cm -1 , indicating its perpendicular orientation to the air-water interface. When BA was added to the subphase, the NH 2 scissoring absorption band from the triaminotriazine moiety disappeared due to the complementary hydrogen bonding of BA to the 2C 18 TAZ monolayer. The formation of the rigid 1:1 hydrogen-bonding network also resulted in the disappearance of one of the ring quadrant stretch absorption bands of the 2C 18 TAZ molecule. New bands which are attributed to the vibration of BA can be clearly seen. Particularly, the CdO stretch from BA shows up in the spectra as two negative absorption bands around 1700 cm -1 . The negative signature of these two bands suggests that the BA molecules are oriented in the hydrogen-bonding network with the C-2 carbonyl positioned vertically toward the air, and the C-4 and C-6 carbonyls directed into the water subphase. This is consistent with formation of an assembly which optimizes the use of complementary hydrogen bonding between two components. Furthermore, the effect of competitive polar organic solvents in subphase, such as DMSO, on the hydrogen-bonding network has also been observed in this study. Compared to the previous IRRAS studies on the similar monolayers, the sensitivity of PM-IRRAS is obviously improved. PM-IRRAS will likely become a powerful analytical technique for the characterization of molecular structure and orientation of Langmuir monolayers at the air-water interface.

show abstract

“…4) [70] . Both melamine and cyanuric acid are easily modified, and these modifications provide the basis for a very simple system with which to study self-assembly, both in molecules in solution, and in the solid state [71][72][73][74][75] .…”

Section: Self-assembly: Derivatives Of Melamine and Cyanuricmentioning

confidence: 99%

Physical‐Organic Chemistry: A Swiss Army Knife

Whitesides

2015

Israel Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

Abstract"Physical-organic chemistry" is the name given to a subfield of chemistry that applies physical-chemical techniques to problems in organic chemistry (especially problems involving reaction mechanisms). "Physical-organic" is, however, also a short-hand term that describes a strategy for exploratory experimental research in a wide range of fields (organic, organometallic, and biological chemistry; surface and materials science; catalysis; and others) in which the key element is the correlation of systematic changes in molecular structure with changes in properties and functions of interest (reactivity, mechanism, physical or biological characteristics). This perspective gives a personal view of the historical development, and of possible future applications, of the physical-organic strategy.

show abstract

The design of organic structures in the solid state: hydrogen-bonded molecular "tapes"

Cited by 239 publications

References 0 publications

Pharmaceutical Co-Crystals

Pharmaceutical Co-Crystals

Polarization-Modulated Infrared Reflection Absorption Spectroscopic Studies of a Hydrogen-Bonding Network at the Air−Water Interface

Physical‐Organic Chemistry: A Swiss Army Knife

Contact Info

Product

Resources

About